04 test pharmaceutical chemistry

PHARMACEUTICAL CHEMISTRY

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Contents

1. Simple Choice .............................................................................................................................2 2. Multiple Choice.........................................................................................................................37 4. Categorization ...........................................................................................................................73 5. Relation analysis........................................................................................................................98 6. Answer Key.............................................................................................................................110


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1. Simple Choice Select the correct answer by marking the appropriate capital letter. There is only one correct answer.

1. Choose the correct definition. Specific absorbance (absorptivity) is:

A. The absorbance of a 1 g/v % solution at a given wavelength. B. The absorbance of a 1 M solution at a given wavelength. C. The absorbance of a 0.001 g/v % solution in 1 cm path length at a given

wavelength. D. The absorbance of a 1 g/v % solution in 1 cm path length at a given wavelength. E. The ratio of the absorbance intensities of two adjacent maxima of the spectrum.

2. Which of the following phenomena is related to UV spectroscopy? A. Excitation of rotations of molecules. B. Excitation of rotations of substituents. C. Excitation of electronic systems of molecules. D. Excitation of outer electrons of light atoms. E. Excitation of internal electrons of atoms.

3. Which of the following phenomena defines the bathochromic effect in electron spectroscopy?

A. An increase in the maximum intensity of the absorption curve. B. A decrease in the maximum intensity of the absorption curve. C. A shift in the absorption maximum towards shorter wavelengths. D. A shift in the absorption maximum towards longer wavelengths. E. The absorption of a mixture at a given wavelength.

4. In UV-VIS spectrophotometry, a wavelength shift is bathochromic and hyperchromic, when:

A. the absorption maximum is shifted to a higher wavelength and its intensity does not

change. B. the absorption maximum is shifted to a higher wavelength and its intensity

decreases. C. the absorption maximum is shifted to a lower wavelength and its intensity

increases. D. the absorption maximum is shifted to a higher wavelength and its intensity

increases. E. the absorption maximum is shifted to a lower wavelength and its intensity

decreases.


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5. Absorbance (A) is defined in terms of the original intensity of the light falling on a cell

(I0) and the reduced intensity transmitted from the cell (I). Which of the following equations is true?

A. A =I

I0

D. A =

-I I

I0

B. I

I 0log = A E. I

I 0log= A

C. A = -I I

I0

6. The Pharmacopoeia prescribes determination of the specific rotation [α λ]

t for lots of pharmaceuticals. Which of the following equations is correct?

A. [ ]B

tλt

λρ

αα

•1•100

= D. [ ]ml 1g/100

cm 1A•1

•1000=

tλt

λ

αα

B. [ ]B

tλt

λρ

αα

•1= E. [ ]

t

tλt

λρ

αα

•1

•100=

C. [ ]B

tλt

λρ

αα

•1

•1000=

where: [ ] t

λα = specific rotation in 10 dm3/kg

αt = rotation measured at t °C, at wavelength λ

l = length of the cell in dm

ρB = mass concentration of substance B in g/0.1 dm3

ρt = density of liquid at t °C

7. Which parts of the polarimeter, if any, should be transposed?

A. 2 and 4 D. 4 and 5

B. 3 and 4 E. The sequence of the parts is correct.

C. 2 and 3

1 2 3 4 5light source polarizer analyzer sample tube observer


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8. Which wavenumber range is prescribed by the Pharmacopoeia for IR measurements?

A. 2.5 – 15 cm-1 D. 670 – 4000 cm-1

B. 60 – 208 cm-1 E. 3800 – 6000 cm-1

C. 206 – 560 cm-1

9. Which of the listed light sources is used in atomic absorption spectroscopy?

A. Tungsten lamp D. NERNST lamp

B. Deuterium lamp E. Hollow cathode lamp

C. Helium-neon-laser

10. Which of the listed purposes is NMR spectroscopy not used for?

A. Structure elucidation and identification (with or without standards)

B. Detection of impurities and decomposition products.

C. Determination of ratio of stereoisomers.

D. Examination of nuclear radiation.

E. Determination of OH, NH and SH protons.

11. Which of the compounds listed below contains a doublet signal in its proton resonance

spectrum? A. ethyl-methylether D. n-hexane

B. acetone E. diisopropylether

C. diethylether

12. Which of the listed chemical shift ranges contains the 13C-NMR signal of carbonyl

groups? A. 160-240 ppm D. 50-60 ppm

B. 250-280 ppm E. 100-120 ppm

C. 10-30 ppm

13. What relation exists between the specific absorption coefficient and the molar

absorption coefficient? A.

D.

B.

E.

C.


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14. Chromophoric groups are those ...

A. in which n → π* and π → π* transitions are possible.

B. which cause the color of the compound.

C. whose electrons are able to absorb energy.

D. which contain excitable sigma-electrons.

E. which donate electrons.

15. The figure shows the UV absorption spectra of a two-component drug mixture. Select

the most appropriate λ values for the measurement using the “two-wavelength” method.

A.

B.

C.

D.

E.

2 and 4

1 and 4

2 and 3

3 and 4

1 and 2

16. The figure shows the UV spectra of the components of “Spiritus salicylatus cum resorcino” and the table contains the related characteristic values. By the help of these data, select the false statements.

A1cm 1% λ=275

A1cm1% λ=297

resorcinol 167 0 salicylic acid 83 250

A. Curve 1 is the spectrum of resorcinol.

B. Curve 1 is the spectrum of salicylic acid.

C. At λ=297 nm salicylic acid can be selectively measured.

D. At λ=275 nm the sum of the absorbances of the compounds can be measured.

E. Both of the components can be determined by spectroscopy using the “two-wavelength” method.

1

2


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17. Which of the following parameters does not influence the conductivity of an

electrolyte? A. The dissociation of the electrolyte.

B. The number of charge-carriers.

C. The temperature.

D. The solvent used.

E. The undissolved electrolyte in case of a saturated solution.

18. The chromatographic Rf value of a substance can be defined as: ...

A. the distance of the spot of the substance from the start, in cm.

B. the distance between the start and the front, in cm.

C. the distance between the spot of the substance and the front, in cm.

D. the distance of the spot of the substance from the start, divided by the distance between the start and the solvent front.

E. the distance between the spot and the start, divided by the total length of the adsorbent layer.

19. Which of the listed terms does not belong to gas-liquid chromatography (GLC)?

A. supporting material D. adsorbent

B. liquid phase E. stationary phase

C. mobile phase

20. Which of the listed electrodes can be used for the amperometric (dead-stop) end-point

detection of a nitritometric titration? A. A glass electrode.

B. A silver electrode.

C. A calomel electrode.

D. A double platinum electrode.

E. A Cl- ion-selective electrode.

21. Tropane alkaloids are separated by TLC on silicagel (stationary phase) with acetone-

water-ammonia eluent. What elution order can be expected based on the structure of the compounds and the chromatographic system applied? (Evaluation from the front to the start; in decreasing RF order.)

A. Apoatropine, atropine, scopolamine.

B. Scopolamine, apoatropine, atropine.

C. Atropine, apoatropine, scopolamine.

D. Scopolamine, atropine and apoatropine together.

E. The compounds are not separated.


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22. Digitalis glycosides (digitoxin, acetyldigitoxin and Lanatoside-C) are separated by TLC on silicagel (stationary phase) with chloroform : ethanol (9:1) eluent. What elution order can be expected based on the structure of the glycosides and the chromatographic system applied? (Evaluation from the front to the start; in decreasing RF order.)

A. The compounds are not separated.

B. Acetyldigitoxin, Lanatoside-C, digitoxin.

C. Digitoxin, acetyldigitoxin, Lanatoside-C.

D. Acetyldigitoxin and digitoxin together, Lanatoside-C.

E. Acetyldigitoxin, digitoxin, Lanatoside-C.

23. What is the correct order of the eluotrope effect of the listed eluents in reversed phase

HPLC? A. water<methanol<acetonitrile<i-propanol

B. i-propanol<acetonitrile<methanol<water

C. methanol<acetonitrile<i-propanol<water

D. water<i-propanol<acetonitrile<methanol

E. water<acetonitrile<i-propanol<methanol

24. Which of the following reactions is not characteristic for ketones?

A. SCHIFF base formation D. oxime formation

B. hydrazone formation E. reaction with silver oxide

C. semicarbazone formation

25. Which of the listed pharmaceuticals is not a hydrocarbon?

A. Benzinum D. Vaselinum album

B. Paraffinum liquidum E. Cetaceum

C. Paraffinum solidum

26. Which of the following compounds does not give a positive phenolic reaction with

iron(III)? A. Mentholum D. Methyldopum

B. Acidum salicylicum E. Methylium salicylicum

C. Morphinium chloratum


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27. The acid value is:

A. The number of acidic groups in an organic compound.

B. The quantity of base expressed in mg of KOH equivalent to the free acid in 1 g of sample.

C. The quantity of KOH in mg needed for neutralization of the free acid in 100 g of sample.

D. A term to characterize the acidity of multibasic acids.

E. A term to express neutralization of the base content of substances.

28. The ester value is:

A. The acid value minus the saponification value.

B. The saponification value minus the acid value.

C. The saponification value plus the acid value.

D. The number of ester groups in 1 mol of a substance.

E. The quantity of KOH, expressed in grams, required to hydrolyze 100 g of an ester derivative.

29. The iodine value is:

A. The quantity of iodine, expressed in g, consumed by 1 g of a fatty

substance.

B. The quantity of halogen, in g, expressed as iodine, consumed by 100 g of a substance (fat, wax).

C. The number of iodine atoms consumed by one molecule of a pharmaceutical.

D. The number of milligrams of iodine formed by oxidation of iodide by 1 g of a pharmaceutical.

E. The number of milligrams of iodine formed by oxidation of iodide by 100 g of a substance.

30. The hydroxyl value is:

A. The number of hydroxyl groups in one molecule of a

pharmaceutical.

B. The number of hydroxyl groups in 1 mol of a substance.

C. The number of milligrams of KOH equivalent to the amount of acetic acid consumed for the acylation of 1 g of a sample.

D. The number of grams of KOH equivalent to the amount of acetic acid consumed for the acylation of 100 g of a substance.

E. The number of milligrams of KOH required for the saponification of a unit amount of an ester.


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31. The SCHÖNIGER method with the use of the SCHÖNIGER flask is appropriate for:

A. Quantitative determination of covalently bound halogen and sulfur

content.

B. Detection of iron and heavy metal content of substances and detection of arsenic.

C. Determination of the nitrogen content of pharmaceuticals.

D. Measurement of the moisture content of pharmaceuticals.

E. Quantitative determination of the acidic character of pharmaceuticals.

32. Which of the listed terms is not a physico-chemical parameter?

A. Melting interval

B. Boiling interval

C. Refractive index

D. Density

E. Saponification value

33. " Evaporate to dryness on water-bath accurately weighed 10 g of sample, then dry the

residue to constant mass at 110oC." Which of the pharmacopoeial tests is described above?

A. Foreign organic substances

B. Loss on drying

C. Sulfated ash

D. Residue on drying

E. Residue on ignition

34. Fill the space with the correct term.

".................: at most 0.5%. Accurately weighed 0.50 g sample is dried in a desiccator above cc. sulfuric acid for 6 hours."

A. sulfated ash

B. loss on drying

C. loss on ignition

D. foreign organic substances

E. test with cc. sulfuric acid


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35. Which of the terms listed below does the definition refer to?

"....................: it is the residue of the substance, expressed in m/m%, obtained by heating with cc. sulfuric acid and consecutive ignition."

A. test with cc. sulfuric acid

B. sulfated ash

C. residue on ignition

D. loss on ignition

E. foreign organic substances

36. Choose the pharmaceutical for which the chemical parameters cited from its monograph

can be characteristic. "Acid value: at most 1 Saponification value: at most 3 Hydroxyl value: 200-220"

A. Acidum oleinicum

B. Adeps solidus

C. Aethylium oleinicum

D. Alcoholum cetylstearylicum

E. Butyrum cacao

37. On the basis of the reaction between iodine and sulfur dioxide, the KARL-FISCHER

method (under appropriate circumstances) is suitable for: A. Determination of the heavy metal content of a pharmaceutical.

B. Simultaneous measurement of the moisture and crystal water content of a pharmaceutical.

C. Measurement of solvent inclusions.

D. Measurement of the oxygen content of solvents and solutions.

E. Detection and measurement of volatile and oxidizable substances.

38. The isoelectric point of a molecule containing both basic and acidic groups is:

A. The potential, measured and expressed in volts, which is required

for the movement of a substance in an electric field.

B. The pH value at which a given amphoteric substance is neutral.

C. The pH value at which a given amphoteric substance exists as a cation.

D. The pH value at which a given amphoteric substance exists as an anion.

E. The electric field at which a given amphoteric substance is neutral.


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39. Choose the correct solution for the quantitative determination of papaverine.

Content of a mixture: Codeinium chloratum Papaverinium chloratum Acidum acetylsalicylicum

A. Alkalization with sodium hydroxide, then titration of the total base content with perchloric acid. Calculation: the equivalent weight of papaverine is calculated from the ratio of molecular weights regarding the theoretical composition.

B. On alkalization with sodium bicarbonate, the papaverine base is released selectively. After extraction into chloroform, it can be titrated with perchloric acid.

C. After alkalization with sodium hydroxide, both bases can be extracted into chloroform, from where papaverine is separated by the addition of an aqueous acidic solution (pH = 2). The solution is made alkaline again, then it is extracted into chloroform, and the papaverine base can be titrated with perchloric acid.

D. From an aqueous acidic solution (pH = 2) the hydrochloric acid salt of papaverine can be extracted into chloroform. After addition of mercury(II)acetate, papaverine is titrated with perchloric acid.

E. After alkalization, both bases can be extracted into chloroform. Codeine, as a strong base, can be titrated directly. After addition of mercury(II)acetate, the papaverine content can also be measured.

40. Which of the following compounds is freely soluble in water?

A. Natrium disulfurosum D. Calcium hydrogenphosphoricum

B. Carbo activatus E. Sulfur praecipitatum

C. Bismuthum subnitricum

41. Choose the false statements related to the general impurity tests of the Pharmacopoeia.

A. Certain cations and anions are tested using chemical reactions. B. The changes observed in these reactions can be: colorization, precipitation (possibly

opalescence). C. The evaluation is based on comparison with reference solution or blank experiment. D. The requirement: “the reaction mixture must not be changed” means, that the

quantity of impurity allowed is under the detection limit. E. If the changes in the sample solution are equal to that of the reference solution, the

substance is qualified as: "it does not meet the requirements".

42. Which of the statements is false for the following reaction applied in Pharmacopoeial impurity tests? 2K2HgBr2I2 + NH3 + 3KOH = HgO. HgNH2I + 3KI + 4KBr + 2H2O

A. It is the reaction equation of the test for ammonia content. B. The reagent is called: MAYER. C. In case of low ammonia concentration yellow color is produced. D. NO3

- content after reduction can also be detected by this reaction (test for NO3- and

NH3). E. The reagent is called: NESSLER-WINKLER.


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43. Which statements is correct for the general impurity tests of the Pharmacopoeia?

A. Always 1g of the sample is examined. B. A reference solution is always used for the evaluation. C. It is a qualitative test. D. It is a quantitative test. E. It is a semiquantitative test.

44. Which of the qualitative tests is carried out according to the following prescription in the monograph of Fructosum? "Dissolve 1.0 g of the substance in 10.00 ml freshly boiled and cooled water, add 2 drops of I-phenolphthalein solution. The solution must be colorless; on addition of 0.30 ml of 0.01 M NaOH, the color must turn red. "

A. Acidity. B. Alkalinity. C. Acidity and alkalinity. D. Insoluble and coloring matter. E. Readily oxidizable substances.

45. Which formula is correct for Natrium disulfurosum? A. Na2S2O2 D. Na2S2O5

B. Na2S2O3 E. Na2S2O8

C. Na2S2O4

46. An ointment contains ephedrine hydrochloride, clioquinol and lidocaine as ingredients.

An aliquot of its alkaline aqueous suspension is extracted with chloroform. Which of the components is measured on titration with perchloric acid in the chloroform phase?

A. ephedrine B. lidocaine C. ephedrine + clioquinol D. lidocaine + ephedrine E. lidocaine + clioquinol

47. An aliquot of the mixture below is refluxed with 10% HCl for 1 hour, then it is titrated with 1M NaNO2 volumetric solution using potentiometric end-point detection. Which of the components is measured? Pulvis antidoloricus: Aethylmorphinium chloratum Coffeinum Phenacetinum Acidum acetylsalicylicum

A. Phenacetin B. Caffeine C. Acetylsalicylic acid D. Ethylmorphine E. None of them


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48. An aliquot of the mixture below is shaken with 10% NaOH, then it is extracted with 70

ml of chloroform. Which of the components is measured on titration with perchloric acid in the chloroform phase using I-tropeoline solution? Pulvis antidoloricus: Aethylmorphinium chloratum Coffeinum Phenacetinum Acidum acetylsalicylicum

A. Caffeine B. Ethylmorphine + caffeine C. Ethylmorphine D. Ethylmorphine + phenacetin E. Caffeine + phenacetin

49. What does it mean? “The adsorption capacity of Carbo activatus is 45%” A. Activated charcoal adsorbs by 45% less amount of phenazone than its mass. B. The content of the pharmaceutical is not less than 45%. C. 45% of phenazone added to the charcoal is adsorbed. D. The amount of the adsorbent charcoal is 45% of the mass of phenazone that can be

adsorbed. E. Not less than 45 g phenazone is adsorbed by 100 g of activated charcoal.

50. Which of the following substances can be identified by the GRIESS-ILOSVAY reagent? A. Natrium dihydrogenphosphoricum B. Calcium carbonicum C. Ammonium bromatum D. Natrium nitrosum E. Hydrogenium peroxydatum

51. Which of the processes listed below is suitable for the synthesis of iodine? A. The SOLVAY process. B. The reduction of the iodide content of artesian waters with sodium thiosulfate. C. The oxidation of iodate with sulfite in alkaline extract obtained after the

crystallization of salpetre (potassium nitrate). D. The oxidation of iodides with chlorine in alkaline extraction of ash obtained from

see plants. E. Catalytic oxidation of periodates with air.

52. Which of the following statements is correct? Natrium nitrosum : A. contains a nitrogen atom of oxidation number (+5). B. upon dropping with cc. sulfuric acid brown nitrous gases are evolved. C. forms an azo dye with sulfanilic acid. D. produces a jelly-like, white precipitate with GRIESS-ILOSVAY reagent. E. undergoes oxidation with zinc to sodium nitrate in acidic solution.


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53. Which of the following pairs are Z-E isomers?

A. butyric acid — isobutyric acid B. ephedrine — pseudoephedrine C. quinine — quinidine D. maleic acid — fumaric acid E. tartaric acid — succinic acid

54. How many chiral carbon atoms can be found in this molecule?

O

HO OH

O

H

H

HO

OH

A.

B.

C.

D.

E.

1

2

3

4

5

55. What do we call an eutomer?

A. The enantiomer of a chiral drug that has higher affinity to the receptor. B. The levorotatory enantiomer of a chiral drug. C. A drug used for euthanasia. D. The R enantiomer of chiral pharmaceuticals assigned according to the Cahn-Ingold-

Prelog convention. E. A chiral pharmaceutical compound that has enantiomers of identical

pharmacological activity.

56. Which of the procedures below is used for the industrial synthesis of sodium hydrogen carbonate?

A. The SOLVAY process B. The HABER-BOSCH process C. The MARSH reaction D. The NESSLER-WINKLER method E. The KOLBE-SCHMIDT synthesis

57. What is the official name of sodium tetraborate in the Ph. Hg. VII.? A. Natrium tetraboricum B. Dinatrium tetraboricum C. Natrium boratum D. Natrium tetraboratum E. Dinatrium tetraboratum


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58. Which of the precipitates listed below is formed in the Ph. Hg. VII. identification

reaction of Calcium hydrogenphosphoricum? A. CaO B. Ca3(PO3)2 C. Ca(COO)2 D. CaCO3 E. Ca(HCOO)2

59. Which statement is false? A. The partition coefficient is the concentration ratio of a compound in the organic and

aqueous phases. B. The partition coefficient depends on temperature and pressure. C. The partition coefficient depends on the concentration of the partitioning substance. D. The partition coefficient is a characteristic physico-chemical parameter of a

compound in a given solvent system. E. The higher the logP value, the more lipophilic the compound is.

60. Which of the following compounds does not exist in ionized form at gastric pH? A. Papaverine B. Ephedrine C. Phenylbutazone D. Aminophenazone E. Morphine

61. Select the injectional narcotic agent from the listed narcotic compounds. A. trichlororethylene B. thiabutabarbital C. dinitrogen oxide D. halothane E. methoxyflurane

62. Which of the following liquids is freely miscible with water? A. Aether B. Alcoholum isopropylicum C. Alcoholum benzylicum D. Chloroformium E. Trichloroaethylenum


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63. Which is the specific impurity of chloroform?

A. furfural B. melubrine C. peroxide D. phosgene E. methanol

64. Select the false statement. A. The morphine impurity of codeine can be detected with sodium nitrite. B. Codeine and ethylmorphine can be differentiated by means of the FEIGL-SILVA

reaction. C. Apomorphine turns blood-red after the addition of concentrated nitric acid. D. Morphine and nalorphine can be differentiated with FeCl3. E. In the non-aqueous acidimetric assay of morphine, all the related alkaloid impurities

are measured simultaneously.

65. Which of the compounds listed below contains a piperidine ring? A. trimetozine B. morphine C. niflumic acid D. naproxen E. ibuprofen

66. The chemical name of apomorphine is: “(-)-(R)-5,6,6a,7-tetrahydro-10,11-dihidroxy-6-methyl-4H-dibenzo[de,g]quinoline”. What does the (-)-(R) prefix mean in the name?

A. It rotates the plain of polarized light to the left and at the assignment of the absolute

configuration the order of the relevant substituents shows counter-clockwise direction.

B. It rotates the plain of polarized light to the left and at the assignment of the absolute configuration the order of the relevant substituents shows clockwise direction.

C. It rotates the plain of polarized light to the right and at the assignment of the absolute configuration the order of the relevant substituents shows counter-clockwise direction.

D. It rotates the plain of polarized light to the right and at the assignment of the absolute configuration the order of the relevant substituents shows clockwise direction.

E. The (R) prefix denotes the racemate form.

67. Select the correct statement for the morphine derivatives. A. Codeine contains a phenolic hydroxyl group. B. Ethylmorphine cannot be extracted from alkaline aqueous solution into chloroform. C. Codeine and ethylmorphine can be distinguished by the ZEISEL reaction. D. Nalorphine contains a quaternary nitrogen atom. E. Codeine is the 3-methyl ether of morphine.


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68. Which of the following statements is correct?

A. Pethidine is a tricyclic morphine derivative. B. Pethidine is a piperidine carboxylic acid derivative. C. Pethidine contains one chiral centre. D. Pethidine contains a quaternary nitrogen. E. Pethidine contains a pyridazine moiety.

69. Which of the following chemical names is correct for Pethidinium chloratum? A. 4,4-diphenyl-2-(dimethyl-ammonio)-5-heptanone-chloride B. 4-(ethoxy-carbonyl)-4-phenyl-1-methyl-piperidinium-chloride C. N-phenyl-N-[1-(2-phenyl-ethyl)-4-piperidinyl]-propionamide D. 3-ethyl-3-phenyl-2,6-piperidinedione E. 4-(3,4,5-trimethoxy-benzoyl)-morpholine

70. Select the correct substituent for the structure of methadone.

C CH2 CH

CH3

RCH5C2

O

A.

B.

C.

D.

E.

–CH3

–CH(CH3)2

–NHCH3

–N(CH3)2

ON

71. Which of the synthetic morphine analogues listed below has this structure?

N

CH3

COOC2H5

A.

B.

C.

D.

E.

pentazocine

levorphanol

methadone

pethidine

diphenoxylate

72. Select the false statement. The therapeutically used barbiturates:

A. are hydrolyzed to monoureids on warming in alkaline medium B. are weak acids due to enol – oxo tautomerism C. are soluble in sodium carbonate solution D. are complex-forming agents due to their several heteroatoms E. exist in various polymorphous forms


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73. Which of the following barbiturates is N-substituted?

A. barbital B. phenobarbital C. amobarbital D. cyclobarbital E. hexobarbital

74. Which is not a lactam-type 1,4-benzodiazepine derivative? A. nitrazepam B. clonazepam C. chlordiazepoxide D. oxazepam E. diazepam

75. Which of the compounds listed below contains a 1,5-benzodiazepine skeleton? A. diazepam B. medazepam C. clobazam D. alprazolam E. oxazepam

76. Which drug has this structure?

N

N

OH

O2N

A.

B.

C.

D.

E.

diazepam

medazepam

nitrazepam

alprazolam

flunitrazepam

77. Select the correct name of the heterocyclic skeleton in the structure of alprazolam.

N

NCl

NNH3C

A.

B.

C.

D.

E.

triazolo[4,3-a][2,3]benzodiazepine



imidazolo[4,3-a][3,1]-benzodiazepine



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78. What type of isomerism exists between cyclobarbital (I) and hexobarbital (II)?

N

NH

O O

O

Et

H

N

NH

O O

O

Me

Me

I II

A. geometric isomers D. tautomers

B. structural isomers E. not isomers of any kind

C. optical isomers

79. Which of the following drugs is a 2,3-benzodiazepine derivative?

A. tofisopam B. chlordiazepoxyde C. medazepam D. diazepam E. midazolam

80. Which heterocyclic moiety does midazolam contain?

N

N

N

Cl

Me

F

A.

B.

C.

D.

E.

Indolizine

Quinolizine

Imidazole

Isoquinoline

Indole

81. The following compounds have common moieties indicative of a therapeutical class.

Which class?

NH

NH

O

OO

H5C2

H5C6

NH

NH

O

O

H5C2

H5C6

NH OO

C6H5

H5C6 O

N OO

CH3

H3C

CH3

NH OO

CH3

H5C2

A. sedatohypnotics B. anxiolytics C. antiepileptics D. antiparkinsonian agents E. antihistamines


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82. Which substituent is present in levomepromazine?

S

N

R

OCH3

R R

A. CH2 CH2 N

CH3

CH3 D. CH2 CH CH2

CH3

N

CH3

CH3

B. CH2 CH CH2

CH3

CH

CH3

CH3

E. CH2 CH2 CH3NNCH2

C. CH2 CH CH2

CH3

N

83. Which of the drugs listed below has the following chemical name: 5-(3-dimethyl-

ammonio-propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-chloride? A. Imipraminium chloratum B. Chlorpromazinium chloratum C. Levomepromazinium hydrogenmaleinicum D. Trifluperidolum chloratum E. Pilocarpinium chloratum

84. Select the false statement for physostigmine? A. It has an eseroline skeleton. B. It is an ester-type alkaloid. C. The acid component of the ester group is dimethylcarbamic acid. D. It contains three nitrogen atoms. E. When made alkaline, its aqueous solution turns red.

85. Which is the false statement for methylhomatropine bromide? A. Its aqueous solution is neutral. B. It is readily soluble in water, and slightly soluble in chloroform. C. The base released from its alkaline aqueous solution can be extracted into

chloroform. D. It gives a precipitate with sodium tetraphenylborate even in slightly alkaline

medium. E. Its alcohol component is methyltropine.


21

86. Which of the following heterocyclic rings forms part of the tropane skeleton?

A. imidazolidine B. pyrazoline C. piperazine D. pyrimidine E. pyrrolidine

87. What is the stereochemical relation between tropine and ψ-tropine? They are: A. enantiomers B. geometric isomers C. conformational isomers D. structural isomers E. tautomers

88. Complete the following sentence with the correct expression: (±)-ephedrine and (±)-pseudoephedrine are ... of each other.

A. structural isomers B. diastereomers C. enantiomers D. tautomers E. conformers

89. The following reactions are performed with a compound: 1. Copper(II) sulfate solution and a small amount of sodium hydroxide are added to its

aqueous solution. The violet product can be extracted into butanol. 2. Sodium hydroxide and potassium hexacyanoferrate(III) solution is added to its

aqueous solution. On heating, the characteristic odor of benzaldehyde is recognizable.

What is the name of the compound?

A. epinephrine B. amphetamine C. ephedrine D. isoprenaline E. pholedrine

90. Which of the following structural elements is characteristic of the β-blockers? A. A quaternary carbon connected to a tertiary nitrogen by two methylene groups. B. Α β-propoxyethyl side chain. C. Α γ-amino-β-hydroxypropoxy side chain. D. A (β-aryl-γ-hydroxypropyl)amino side chain. E. A tropane skeleton.


22

91. Which of the following compounds is the starting material in the synthesis of

oxprenolol? A. resorcinol B. pyrogallol C. hydroquinone D. pyrocatechol E. phloroglucinol

92. Choose the characteristic side chain connected to the aromatic moiety of β-receptor blockers.

A. CH2 CH

OH

CH2 NH CH(CH3)2

B. O CH2 CH2 CH2 NH CH(CH3)2 C. O CH2 CH

OH

CH2 NH R

D. O CH CH2 CH2 NH R

OH E. O CH2 CH CH2 NH CH(CH3)2

OH

93. Which of the following compounds is the starting material in the synthesis of tolazoline? A. ethyl acetoacetate B. glutaraldehyde C. phenylhydrazine D. epichlorohydrin E. ethylenediamine

94. Select the correct name for the structure:

N

NH2

NH

A. guanoside B. debrisoquine C. guanoxan D. terbutaline E. guanethidine

95. Choose the right statement. Captopril is an N-acylated derivative of ……….. A. phenylalanine B. histidine C. leucine D. proline E. tryptophane


23

96. Complete the following sentence with the correct text.

In an acidic solution of Cocainium chloratum,……on the action of dichromate. A. the N-methyl group will be oxidized to carboxylic acid B. the methoxycarbonyl group will be reduced to aldehyde C. the benzoyl ester group will be hydrolyzed D. an orange-red precipitate will be formed E. free cocaine base will precipitate out as a white solid

97. Complete the following sentence with the correct text. Structure-activity investigations of cocaine revealed that:

A. the local anaesthetic effect of cocaine is due to its molecular association. B. the local anaesthetic effect does not necessitate all of the molecular moieties of

cocaine. C. for the optimum effect, cocaine needs further ester functions in its structure. D. for the activity, exclusively the presence of the methyl and quinuclidine moieties is

desired. E. a good anaesthetic effect develops only if the distance between the two nitrogens of

the cocaine skeleton is four carbon atoms (around 0,5 Å).

98. Select the false statement. In synthetic local anaesthetics: A. a lipophilic (aromatic) moiety, a linking chain and a hydrophilic dialkylamine part

can generally be found. B. the stability of amides is higher than that of esters. C. the percentage ionized form of procaine, tetracaine and lidocaine significantly

predominates that of the non-ionized one at tissue pH. D. benzocaine and procaine can be distinguished with diazonium-salt formation

reaction. E. tetracaine can be measured as a bivalent base in non-aqueous medium.

99. Which of the following reactions occur in the bromatometric assay of benzocaine? A. electrophilic addition B. nucleophilic addition C. elimination D. electrophilic substitution E. nucleophilic substitution


24

100. There are three nitrogens in procainamide. Characterize the sequence of their basic

strength.

H2N C NH CH2 CH2 NC2H5

C2H5

O

1 2 3

A. N1 < N2 < N3 B. N1 = N2 < N3 C. N2 < N3 < N1 D. N2 << N1<< N3 E. N2 < N1 = N3

101. Which of the following statements is false for quinidine? A. It is an antiarrhythmic agent. B. It has rubane ring skeleton. C. It contains a quinoline and a quinuclidine ring. D. It is the enantiomer of quinine. E. It is the diastereomer of quinine.

102. Complete the following sentence. Diltiazem has a .........skeleton.

A.

B.

C.

D.

E.

benzodiazepine

benzothiazepine

benzothiazine

benzothiadiazine

phenothiazine

N

S

OCH3

OCH3

OO

NH3CCH3

103. Which drug has this structure?

NHH3C CH3

H3COOC COOCH3

HO2N

A.

B.

C.

D.

E.

isosorbide dinitrate

nifedipine

prenylamine

phendylium

lidoflazine


25

104. Which of the following substances gives a positive murexide reaction?

A. carbromal B. vincamine C. methylhomatropine D. nitrofurantoin E. xanthinol nicotinate

105. Which of the following drugs is not a nitro compound? A. chloramphenicol B. nifedipine C. nitrazepam D. nitroglycerine E. nitrofurantoin

106. Which is the structure of methyldopa?

A. HO

HO

CH2 C

CH3

COOH

NH2

D. HO

HO

CH2 CH

NH2

COOH

B. HO

HO

CH2 CH2 NH2

E. HO CH2 CH

CH3

NHCH3

C. HO

HO

CH

OH

CH2 NHCH3

107. Which of the compounds listed below is a 3,4-dihydroisoquinoline derivative?

A. drotaverinium chloride B. bencyclane hydrogen fumarate C. papaverine chloride D. noscapine chloride E. apomorphine

108. Which of the following compounds does not contain an ester function? A. acetylsalicylic acid B. lidocaine C. scopolamine D. benzocaine E. cocaine


26

109. Which of the following statements is not correct for this structure?

COOH

C

C

COOH

H OH

HO H

A.

B.

C.

D.

E.

Official as Acidum tartaricum in Pharmacopoeia .

It contains two asymmetric centres.

Its configuration is erythro.

On heating it melts, then carbonifies and burns without a residue.

When H2O2 and FeSO4 are added to its alkaline solution, a bluish-violet complex forms.

110. What is the name of this compound?

CH3

CH3

HOH

OH

OHH3C

HOOC

A.

B.

C.

D.

E.

cholanic acid

cholic acid

lithocholic acid

dehydrocholic acid

deoxycholic acid

111. Which compound has this structure?

A.

B.

C.

D.

E.

colecalciferol

ergocalciferol

cholic acid

ergosterol

cholesterol

H

H H

HO

112. Which of the following steroid skeletons contains the largest number of carbon atoms?

A. androstane B. cholane C. estrane D. pregnane E. perhydrocyclopenta[α]-phenantrane

113. Which statement does not fit the structure of natural androgens? A. They are derivatives of 10,13-dimethylsterane. B. Two double bonds can be found in ring A of the sterane skeleton. C. There is a OH or an =O group on C3. D. There is a OH or an =O group on C17. E. The anellation of the rings is trans.


27

114. Which natural androgen has this structure?

CH3

CH3

O

H H

OH

HH

A.

B.

C.

D.

E.

androsterone

ethisterone

testosterone

dehydroepiandrosterone

methanedienone

115. Which of the following groups of steroids contains an aromatic ring A?

A. estrogens B. androgens C. progestins D. glucocorticoids E. mineralocorticoids

116. Which is the C17 substituent of progesterone? CH3

CH3

O

H H

R

H

A.

B.

C.

D.

E.

=O

–OH

–CH2–CO–CH3

–CO–CH3

–CO–CH2OH

117. Which is the characteristic C17 side chain in corticosteroids?

A. CH2 CH2 OH

D. CO

CH3

B. CO

CH2CH3 E. CH

CH2CH2COOH

CH3

C. CO

CH2OH

118. Which compound is shown?

C

CH3

O

H H

H

HO

O H C

CH2OH

OH

A.

B.

C.

D.

E.

corticosterone

deoxycorticosterone

hydrocortisone

prednisolone

aldosterone


28

119. Which is the C21 substituent of mazipredone?

A. morpholinyl B. piperidyl C. N-methylpiperazinyl D. 1,4-oxazinyl E. isoquinolyl

120. Which of the structural modifications listed below increases the antiinflammatory effect of hydrocortisone?

A. Elimination of the C17 side chain. B. Appearance of a ∆1,2 double bond. C. Formation of 11-deoxy derivative. D. Aromatization of ring A. E. Reduction of the C3 carbonyl group.

121. Which is a natural corticosteroid hormone? A. prednisolone B. mazipredone C. triamcinolone D. hydrocortisone E. prednisone

122. Which is false for prostaglandins? A. They are monocarboxylic acid derivatives containing 20 carbon atoms. B. They are formed from arachidonic acid in the body. C. Their acidic character is due to phenolic hydroxyl groups. D. They can be classified based on their alycyclic moiety. E. At least one chiral C atom is present in their structure.

123. Which is correct? A. Ring A of prednisolone contains two double bonds. B. Prednisolone has an androstane skeleton. C. Prednisolone contains a piperazine ring. D. Prednisolone is a mineralocorticoid. E. There is an ester group in its structure.

124. What is the name of this "highly active" diuretic drug?

Cl

H2NO2S

NH

COOH

O

A.

B.

C.

D.

E.

acetazolamide

clopamide

furosemide

chlorthalidone

ethacrynic acid


29

125. Which chemical name belongs to aminophylline?

A. 2-aminotheophylline B. 3-aminohexahydrobenzoxazine C. salt of ethylenediamine and theophylline D. 6-aminotheophylline E. ammonium theophyllinate

126. Complete the following sentence with the correct text. Xanthine exists in two tautomeric forms, in …... equilibrium.

A. diendo-diexo B. alloxanthine-isoalloxanthine C. keto-enol D. meso-pseudo E. lactam-lactim

127. Which statement is false for spironolactone? A. It is a pentacyclic compound. B. It is a synthetic steroid derivative. C. There is a butyrolactone ring in its structure. D. It is produced by a Spirochaeta species. E. There is an acetylthio moiety on its skeleton.

128. Select the proper solution of the equation below.

+ 5 NaIO4

CH2OH

CH OH

CHO H

CH OH

CH OH

CH2OH

A.

B.

C.

D.

E.

6 HCOOH + 5 NaIO3

4 CH2O + 2 HCOOH + H2O

2 CH2O + 4 HCOOH + H2O

2 CH2O + 4 HCOOH + 5 NaIO3 + H2O

2 CH2O + 4 HCOOH + 5 NaIO3


Glycerol: A. is a tertiary alcohol. B. is freely miscible with water. C. enol-oxo tautomerism can occur in its molecule. D. its D and L isomers have been selected by EMIL FISCHER as the reference molecules

in the representation of configuration. E. on heating with phosphoric acid the odor of acridine is recognizable.


30

130. Which of the following substances is not a polypeptide?

A. ACTH B. angiotensin C. endorphin D. insulin E. thyroxine

131. Which is the correct chemical name of methimazole?

N

N

CH3

HS

A.

B.

C.

D.

E.

2-mercapto-3-methylimidazole

1-methyl-2-thioxypyrimidine

1-methyl-2-mercaptoimidazolidine

2-mercapto-1-methylimidazole

2-mercapto-3-methylimidazoline

132. Which statement is false for insulin?

A. Human insulin differs from porcine insulin in merely one amino acid. B. Its structure is built up by 16 different amino acids. C. Two shorter peptides (A and B) form insulin. D. A and B peptides are linked by disulfide bridges in the structure of insulin. E. Its isoelectric point is in the alkaline pH range.

133. Which is the false statement referring to the molecule with the structure below?

Cl SO2 NH C

O

NH

A. It is an oral antidiabetic. B. It is a non-chiral molecule. C. It can be applied in insulin-deficient diabetes. D. It has a sulfonyl-carbamide structure. E. It was prepared by Hungarian researchers.

134. Choose the wrong statement. α-Tocopherol... A. has a cromane skeleton. B. contains a phenolic function. C. is sensitive to oxidation. D. plays an antioxidant role in the organism. E. is a colorless or pale-yellow crystalline powder.


31

135. Which of the following amino acids is a building moiety of panthotenic acid (Vit. B5)?

A. β-alanine B. glycine C. 4-amino-3,3-dimethylbutyric acid D. γ-aminobutyric acid E. p-aminobenzoic acid

136. Which name does not correspond to vitamin C? A. ascorbic acid B. 2-keto-L-gulonic-γ-lactone C. antiscurvy factor D. 2-keto-L-gluconic acid E. (+)-(1'R,4R)-2,3-dihydroxy-4-(1',2'-dihydroxyethyl)-2-pentene-4-olide

137. Which of the statements referring to ascorbic acid is false? A. It has a strong reducing ability. B. Its acidic character is a consequence of the endiol structure. C. Its oxidation product is dehydroascorbic acid. D. It has no asymmetric centre. E. It absorbs light strongly in the UV region.

138. Which property of ascorbic acid is not related to the endiol structure? A. It can be determined with bromatometry. B. It can be determined with alkalimetry. C. It is dextrorotatory. D. It forms a complex with Fe2+ ions in slightly alkaline medium. E. Its UV spectrum is pH-dependent.

139. Complete the following sentence with the correct text.

Lactose and saccharose are:…….. A. geometric isomers B. diastereomers C. enantiomers D. structural isomers E. not isomers of any kind

140. What is the chemical structure of calcium (+)-D-gluconate? A. A polyhydroxy complex of D-glucose and calcium salts. B. The product of neutralization of levorotatory gluconic acid with calcium carbonate. C. The calcium salt of dextrorotatory D-gluconic acid. D. The calcium salt of glucuronic acid. E. The calcium complex of L-gulonic acid glucoside.


32

141. Select the false statement referring to the compound below.

NN

H O

O

H3C

O

A.

B.

C.

D.

E.

It contains two lactam groups.

Three carbonyl groups can be found in it.

It has a pyrazolidinedione skeleton.

It contains two basic nitrogens.

It contains an active C4 hydrogen.

142. Which of the statements is false for phenylbutazone?

A. In its structure a butyl group is coupled also to the basic skeleton. B. It has acidic character. C. On hydrolysis monohydrazide derivatives are formed from phenylbutazone. D. One of the starting materials of its synthesis is diethyl malonate. E. In its heterocyclic skeleton C4 is chiral.

143. Which of the following heterocyclic rings is the basic skeleton of phenylbutazone? A. pyrazolidine B. pyrrolidine C. piperazine D. diazetidine E. pyridazine

144. Name the parent compound of diclofenac. A. anthranilic acid B. phenylacetic acid C. indolylacetic acid D. arylpropionic acid E. other

145. Which of the following heterocyclic structures is the basic skeleton of piroxicam?

SN

O

N N

OH

Me

OO

H

A.

B.

C.

D.

E.

phenothiazine

1,3-benzothiazepine

1,2-benzothiazine

benzothiasole

benzene


33


A. Indomethacin is an antiinflammatory drug with a pyrazolidinedione skeleton. B. Indomethacin contains a basic nitrogen. C. Indomethacin contains an m-chlorophenyl substituent. D. Indomethacin is an acylated indolylacetic acid derivative. E. Indomethacin has good water-solubility because it contains a basic nitrogen.

147. Which is correct for the non-steroidal antiinflammatory anthranilic acid derivatives? A. Drugs of this class are N-aryl derivatives of anthranilic acid. B. Drugs of this class are N-aryl derivatives of the ethyl ester of anthranilic acid. C. Drugs of this class are N-cycloalkyl derivatives of anthranilic acid. D. Drugs of this class are N-alkyl derivatives of anthranilic acid. E. Drugs of this class are N-alkyl derivatives of the ethyl ester of anthranilic acid.

148. Which of the following drugs has the chemical name:

"2-[3-(trifluoromethyl)-anilino]-nicotinic acid"? A. naproxen B. ketamine C. paracetamol D. niflumic acid E. meprobamate

149. Substitute the appropriate answer for the phenindamine base. It is a(n) ………… derivative.

N CH3

A.

B.

C.

D.

E.

indane

quinoline

pyridindene

indole

benzopyridine


A. Histamine is a basic amino acid. B. Histamine contains a pyrazole ring. C. Histamine is formed from histidine in the tissues by the action of angiotensin II. D. The guanidino group of histamine is protonated at the pH of the blood. E. Histamine forms a red azo dye with diazotized sulfanilic acid.


34

151. Which statement is correct?

A. On bromination of phenol 3,4,5-tribromophenol is formed. B. Phenol can be determined quantitatively by addition of bromine. C. Phenol has a strong acidic character. D. The equivalent mass of phenol is Et=M/6 in the bromatometric assay. E. The trivial name of 1,4-dihydroxybenzene is resorcinol.

152. Which of the following compounds is not a bicyclic molecule? A. camphor B. methenamine C. cocaine D. trantheline E. homatropine

153. Select the false statement referring to the Cinchona alkaloids. A. There is a great difference between the basicity of the two nitrogens. B. Epiquinine has no antimalarial activity. C. The vinyl group of quinine can be saturated with bromine. D. Dihydroquinine has no antimalarial activity. E. Quinine and quinidine are diastereomers.

154. What stereoisomerism exists between quinine and quinidine? They are: A. enantiomers B. diastereomers C. tautomers D. epimers E. structural isomers

155. Which of the following statements is correct for chloroquine? A. It is an aminoisoquinoline derivative. B. It contains a quaternary nitrogen. C. It is an aminoquinoline derivative. D. The aromatic ring carries two chlorine atom substituents. E. It contains two nitrogens.

156. Which of the following statements is correct for tetracyclines? A. Two of the linearly fused rings have an aromatic character. B. They contain only alcoholic hydroxyl groups. C. They have an amphoteric character. D. They contain a quaternary nitrogen. E. They contain a free carboxyl group.


35

157. Which of the following statements is correct for chloramphenicol?

A. It has four diastereomers. B. It contains a 1,2-aminoalcohol moiety. C. Both of its nitrogens are basic. D. It has cis or trans isomers. E. It contains one alcoholic hydroxyl group.

158. Which of the following chemotherapeutics contains a hydroxyethyl side chain? A. nalidixic acid B. metronidazole C. oxolinic acid D. nitrofurantoin E. furazolidone

159. Which of the following drugs has the chemical name: “1-(2'-hydroxyethyl)-2-methyl-5-nitro-imidazole”?

A. clotrimazole B. nitrofurantoin C. ketoconazole D. metronidazole E. miconazole

160. Which of the following fluoroquinolones contains a chiral centre? A. ciprofloxacin B. norfloxacin C. ofloxacin D. pefloxacin E. enoxacin

NN

HN

N

OH

O

C2H5

F

OE.

N

HN

N

OH

O

F

OA.

N

HN

N

OH

O

C2H5

F

OB.

N

N

N

OH

O

F

O

OCH3H3C

C.

N

N

N

OH

O

C2H5

F

OD.

H3C


36

161. From which of the heterocycles listed below can cycloserine be derived?

A. oxazole B. isoxazolidine C. oxazolidine D. oxazine E. morpholine

162. Which of the following drugs has the chemical name: "R-(+)-4-amino-3-isoxazolidinone"?

A. chlorzoxazon B. acetazolamide C. biotin (Vit. B7) D. cycloserine E. ethosuximide

163. Complete the sentence. Carboplatin is a(n) …….. derivative? A. oxalic acid B. cis-1,2-cyclohexanedicarboxylic acid C. succinic acid D. salicylic acid E. 1,1-cyclobutanedicarboxylic acid

164. Which of the following cytostatics is an alkylating agent? A. cyclophosphamide B. colchicine C. mercaptopurine D. methotrexate E. vinblastine

165. Which of the following cytostatics is a nitrogen mustard derivative? A. melphalan B. busulfan C. mitobronitol D. methotrexate E. carboplatin


37

2 . Mult iple Choice

The following questions have one or more correct answers. Use the notations given below:

A: Only answer 1 is correct. B: Only answer 3 is correct. C: Only answers 1 and 5 are correct. D: Only answers 2 and 3 are correct. E: Only answers 2 and 4 are correct.

166. Which of the following structures have UV absorption that is suitable for quantitative determination as well?

HO

OH

OH

COOH

5.

HO

O

1.

HO

OH

2.

HO

O O

3.HO

OH

4.


38

167. Which of the following functional groups are auxochrome ones in UV spectroscopy?

1. –NH2 2. –C=O 3. –N=N– 4. –C=CH– 5. –OH

168. Choose the compounds whose UV spectrum shows a significant shift upon alkalization.

NH

NH

O

O O

H5C2

H5C2

O

HO

H3CO

N CH3

4.5.

HN CH3

O

OC2H5

COOH

OH

N

H3CO

H3CO

OCH3

OCH3

1.

2.

3.

169. In a UV spectrophotometric assay, the content of a substance can be calculated using the following data:

1. measured absorbance, specific absorption coefficient, path length of the cell 2. measured absorbance, path length of the cell 3. measured absorbance, wavelength of the measurement 4. measured absorbance, molecular weight 5. molar absorption coefficient, measured absorbance, path length of the cell

170. A compound containing an isolated keto group is inactive in UV spectroscopy. However, a well measurable (UV active) derivative is obtained on:

1. reaction with NaBH4 2. reaction with phenylhydrazine 3. reaction with iron(III)-chloride 4. reaction with thiosemicarbazide 5. reaction with Fehling reagent

171 Which of the following substances have an absorption maximum above 220 nm? 1. cyclohexene 2. cyclohexanone 3. cyclohexanol 4. 1,3-cyclohexadiene 5. cyclohexyl methyl ether


39

172. If the Lambert-Beer law is valid, the molar absorption coefficient depends on:

1. the concentration of the absorbing substance. 2. the molecular structure of the absorbing substance. 3. the wavelength of the light used. 4. the thickness of the cell. 5. the thickness of the slit.

173. Which of the following spectroscopic methods measure the light emitted by atoms or molecules?

1. IR spectroscopy 2. flame photometry 3. atomic absorption spectroscopy 4. fluorimetry 5. UV and visible spectroscopy

174. Which of the following statements are correct for the UV spectroscopic assay of a two-component system?

1. The two components of the mixture can be determined at one wavelength if their

specific absorbances are known. 2. The two components of the mixture can be determined at two wavelengths if their

specific absorbances are known. 3. The two components of the mixture can be determined at one wavelength provided

the concentration of one of them is known from another assay. 4. The condition of the determination of the two compounds is that one of them must

have selective absorption. 5. The two components can be determined only if both have selective absorption.

175. Which of the following statements are correct for the spectrophotometric assay of progesterone in an oily injection containing estradiol benzoate and benzylalcohol as well?

1. UV spectroscopy cannot be used because the three components have highly

overlapping absorption spectra. 2. The absorption of progesterone at λ= 240 nm can be eliminated by reduction with

sodium borohydride. 3. The absorbance of the solution reduced with sodium borohydride is measured at

λ=240 nm against an aliquot of the original (not reduced) solution. 4. The absorbance of an aliquot of the original solution is measured at λ=240 nm

against a solution reduced with sodium borohydride. 5. The application of difference-spectrophotometry is impossible because none of the

spectra of the substances is pH-dependent.


40

176. Which of the following statements are correct?

The IR spectrum of a substance can be measured in: 1. a potassium bromide disk. 2. aqueous solution in a glass cell. 3. solid state, in the form of powder. 4. methanol, in a quartz cell. 5. the form of a film between two sodium chloride plates.

177. Potentiometric end-point detection is preferred to conventional visual end-point detection in:

1. non-aqueous titrations of high-resistance solutions. 2. turbid solutions. 3. dead-stop titrations. 4. colored solutions. 5. non-stoichiometric reactions.

178. Which statements apply to potentiometric titrations? 1. The current of the cell is measured against the volume of titrant. 2. The electromotive force of the cell is measured against the volume of titrant. 3. The potential of the indicator electrode is measured directly. 4. The use of a supporting electrolyte is beneficial to increase the conductance in the

case of non-aqueous and very dilute aqueous solutions. 5. The concentration of the substance being determined is computed with the use of a

calibration curve.

179. The figure shows an amperometric titration curve. Which statements apply to this type of curve?

I

ml

1. The substance being determined is electroactive, while the titrant is inactive. 2. The substance being determined is inactive, while the titrant is electroactive. 3. Both the substance being determined and the titrant are electroactive. 4. The equivalence point is at the intersection of the two lines. 5. The potential of the cell is denoted by I, while the volume of the titrant is indicated

in ml on the horizontal axis.


41

180. In water content determination with the KARL FISCHER method, biamperometric end-

point detection is most frequently used. Which statements apply to this type of measurements?

1. A double platinum electrode is immersed into the cell. 2. Two electrodes, a platinum and a calomel are immersed into the cell. 3. While water is present in the solution it reacts with the titrant and current flows

through the cell. 4. The potential difference between the electrodes is registered as a function of the

KARL FISCHER titrant consumption. 5. The current, flowing through the cell is registered as a function of the KARL

FISCHER titrant consumption.

181. A calomel electrode contains: 1. Hg/HgCl2 2. a buffer solution with a suitable pH 3. Hg/ Hg2Cl2/ KCl 4. a solution of NaCl 5. Ag/AgCl

182. Select the false procedures in an instrumental pH measurement. 1. The substance is dissolved in distilled water that was not boiled for a few minutes

and cooled before use. 2. The solution is stirred during the measurement. 3. The correct function of the electrode is validated using two buffer solutions. 4. The combined glass electrode is stored in a pH 7 buffer between measurements. 5. After a long-term storage, the glass electrode is immersed in dilute acid for 24 hours

before measurement.

183. Which of the following statements are correct for proton resonance spectroscopy? 1. The chemical shift of protons in unsaturated functional groups is generally higher

than that of aliphatic protons. 2. In heteroaromatic systems, the chemical shift of the protons adjacent to the

heteroatom is generally lower than that of farther aromatic protons. 3. The protons of benzene derivatives substituted at meta position give a single singlet

signal. 4. The signal of aldehyde protons can be found in range 2-4 ppm. 5. The intensity of spin-spin interaction is characterized by coupling constants.

184. Which of the following signals can be found in the 1H-NMR spectrum of diethyl ether? 1. singlet 2. triplet 3. doublet 4. quartet 5. multiplet


42

185. What are the pharmacopoeial criteria of identity in a gas-chromatographic examination?

1. The retention time of the sample should agree with the value given in the

monograph. 2. The retention time of the sample is equal to that of an identical reference standard. 3. The corrected retention time (tR-tO) of the sample should agree with the value given

in the monograph. 4. The sample and the identical reference standard injected at the same time must give

only one peak. 5. The ratio of the retention time of the sample and the dead time must fall within a

given interval.

186. Select the false statements for the pharmacopoieal HPLC and GC examinations. 1. The peak area can be determined only with an electronic integrator. 2. The area under the peak is proportional to the amount of substance injected and the

sensitivity factor of the detector. 3. With the use of a calibration curve quantitative evaluation can be performed by peak

height measurement if the peak is symmetrical. 4. The amount of the substance is proportional to the product of the peak height and

width measured at the base of the peak, and the symmetry factor is between 0.95 and 1.05.

5. The peak area can only be determined with an electronic integrator when the value of the symmetry factor is between 0.95 and 1.05.

187. Four isomers of C4H9OH are to be separated by GC. Which of the following factors

influence the separation? 1. The type of the detector. 2. The polarity of the stationary phase. 3. The temperature of the column. 4. The quality of the eluent gas applied. 5. The outgoing pressure of the eluent gas.

188. Non-dissociable substances (e.g. caffeine, phenacetin) are separated by HPLC. What kind of chromatographic system can be used?

1. chemically bonded octadecyl-silica gel; methanol 2. chemically bonded octadecyl-silica gel; methanol + water mixture 3. silica gel; pentane 4. chemically bonded octyl-silica gel; acetonitrile + water mixture 5. silica gel; pentane + chloroform


43

189. Corticosteroids (hydrocortisone, cortisone, hydrocortisone acetate, cortisone acetate) are

separated by TLC using silica gel as stationary; chloroform:acetone (3:1) as mobile phase. Which of the statements are correct for the retention order?

1. The ester derivatives have lower RF values than the corresponding corticosteroids. 2. The ester derivatives have higher RF values than the corresponding corticosteroids. 3. Hydrocortisone with its ester and cortisone with its ester produce one spot on the

layer respectively. 4. Cortisone migrates with higher RF value than hydrocortisone. 5. Steroids can be chromatografied only in reversed phase systems.

190. Which of the data listed below are not suitable to define the chromatographic retention? 1. So= the adsorption energy of the solute 2. Rf = retention factor 3. RM = retention parameter 4. k= capacity ratio 5. tR = retention time

191. Select the essential steps in a TLC procedure. 1. Activation of the layer. 2. Application of the substance. 3. Saturation of the chamber. 4. Development of the chromatogram. 5. Spraying with reagent.

192. Which of the listed substances are not used as a TLC stationary phase? 1. silica gel 2. alumina 3. barium sulfate 4. cellulose powder 5. silanized silica

193. Which of the following investigations can be listed in paragraph “Qualitative tests” of a pharmacopoeial monograph?

1. Test for melting interval. 2. Test for insoluble and coloring matter. 3. pH measurement. 4. Description of the macroscopic properties of the substance. 5. Determination of specific rotation.


44

194. Select the chemical parameters from the following pharmacopoeial data.

1. saponification value 2. specific rotation 3. density 4. boiling interval 5. peroxide value

195. Choose the correct statements.

1.

2.

3.

4.

5.

The apparatus is used for the limit test of nitrate-ammonia impurity.

The apparatus is used for the limit test of arsenic impurity.

The tested impurity can be quantitatively determined using this apparatus.

Reduction is performed with hydrochloric acid and zinc added into the flask.

Reduction is performed with the help of DEWARDA alloy and sodium hydroxide added into the flask.

196. Which of the following statements are true?

Natrium hydrogencarbonicum ... 1. bubbles upon dropping with hydrochloric acid. 2. is produced by the HABER-BOSCH process. 3. gives sodium sulfate, white precipitate, upon heating with magnesium sulfate

solution. 4. decolorizes the iodine solution. 5. its aqueous solution is colorless after addition of phenolphthalein.

197. Which statements are true relating to the general impurity tests of Ph. Hg. VII.? 1. The determination of arsenic impurity is carried out by the MARSH probe. 2. In the iron impurity test reaction bromine water forms a blood-red complex with

thiocyanate ions. 3. A possible determination of ammonia impurity is based on the reaction of

ammonium ions with NESSLER-WINKLER reagent giving the solution a brownish-red color.

4. Lead impurity is detected as lead cyanide in the form of a black precipitate. 5. In the nitrate impurity test nitrogen dioxide formed by reduction of nitrate ions gives

a dark brown complex with iron(III) ions.


45

198. Choose the reagents that are not needed in the lead impurity test of Ph. Hg. VII..

1. NH4Cl 2. M HCl 3. R - Na2S 4. 1% ascorbic acid solution 5. M KCN

199. Which statements are correct relating to the lead impurity test of Ph. Hg. VII.? 1. Lead ions are detected as PbS in alkaline medium. 2. KSCN auxiliary reagent is applied to mask copper, iron and zinc ions. 3. In the lead impurity test Fe2+ ion is oxidized to Fe3+ ion with ascorbic acid. 4. Apart from lead ions bismuth ions also give the reaction. 5. The colloidal lead sulfide precipitate gives the solution a yellowish-brown color.

200. Choose the compounds whose assay is based on a redox reaction in Ph. Hg. VII.. 1. Dinatrium hydrogenphosphoricum 2. Kalium bromatum 3. Bismuthum subnitricum 4. Kalium iodatum 5. Lithium carbonicum

201. Which statements are true relating to the adsorption capacity determination of Carbo activatus in Ph. Hg. VII. ?

1. Phenazone is added in known quantity to active carbon and the non-adsorbed

proportion of it is measured. 2. The determination is based on the bromine addition of phenazone. 3. Phenazone has a pyrrole nucleus. 4. The phenazone excess is titrated with potassium bromide. 5. The end-point of the titration can be detected by the disappearance of the blue color

of the iodine-starch complex.

202. Which statements are true both for Natrium disulfurosum and Natrium thiosulfuricum? 1. Its aqueous solution decolorizes the iodine solution. 2. When putting it into a Bunsen flame the substance melts, then catches fire. 3. The pH of its aqueous solution is basic. 4. On acidifying its aqueous solution with hydrochloric acid sulfur precipitates in some

seconds. 5. A sample of the substance wetted with hydrochloric acid imparts the non-

illuminating flame an intense yellow color.


46

203. Which of the following compounds are starting materials in the SOLVAY process of soda

production? 1. sodium sulfate 2. ammonia 3. sodium chloride 4. carbon monoxide 5. hydrochloric acid

204. Which of the following compounds give a precipitate with silver nitrate in neutral medium?

1. Natrium tetraboricum 2. Kalium bromatum 3. Bismuthum subnitricum 4. Dinatrium hydrogenphosphoricum 5. Kalium nitricum

205. Which of the following compounds form a SCHIFF base with p-nitrobenzaldehyde? 1. amphetamine 2. phenindamine 3. prenylamine 4. scopolamine 5. tripelennamine

206. Which statements are true for glacial acetic acid as a non-aqueous solvent? 1. The strength of organic acids dissolved in it increases. 2. The strength of bases dissolved in it increases and the difference between them

decreases. 3. Sulfuric acid behaves as a bivalent acid in glacial acetic acid medium. 4. Perchloric acid behaves as a strong acid in glacial acetic acid medium. 5. In glacial acetic acid, the haloide salts of bases can directly be determined.

207. Choose the compounds that are actually determined in the two titrations given below.

Pil. coffobarbitali: Phenobarbitalum Coffeinum Natrium bicarbonicum Vehiculum

2 pills are dispersed in a small amount of water and dissolved in acetic anhydride by heating, then titrated with perchloric acid using I-tropeoline (first titration). Titration is resumed after adding I-methyl violet indicator to the solution (second titration).

First titration: 1. phenobarbital 2. sodium bicarbonate Second titration: 3. caffeine + phenobarbital 4. caffeine 5. Phenobarbital


47

208. Which statements are correct for a possible assay of a tablet containing

methylhomatropine bromide, phenobarbital and papaverine chloride?

1. The alkalimetric determination of phenobarbital in alcoholic medium is not disturbed by the other components.

2. From alkaline medium papaverine can selectively be extracted to chloroform and titrated with perchloric acid in the organic solvent.

3. The argentometric determination of phenobarbital cannot be used due to the disturbing effect of the haloide salts.

4. Having determined the haloides in acidic medium by argentometry, phenobarbital can be measured in alkaline medium with silver nitrate solution.

5. In acidic medium only methylhomatropine gives a precipitate with sodium tetraphenylborate.

209. Which statements are false relating to the titration of quinine sulfate with perchloric

acid in glacial acetic acid medium? 1. Quinine sulfate contains four basic N atoms altogether. 2. In glacial acetic acid, sulfuric acid protonates one of the quinuclidine N atoms. 3. The titration can only be carried out in the presence of mercury(II) acetate. 4. The equivalent mass is one third of the molar mass. 5. The molecule can be titrated in glacial acetic acid as a trivalent base.

210. Choose the powder mixture whose non-aqueous assay is correctly described in the following sentence. “In a mixture of benzene and glacial acetic acid only aminophenazone is titrated with perchloric acid, the other component does not disturb the determination.”

1. aminophenazone + benzocaine 2. aminophenazone + caffeine 3. aminophenazone + acetylsalicylic acid 4. aminophenazone + lidocaine 5. aminophenazone + ethylmorphine

211. Choose the powder mixtures whose non-aqueous assay is correctly described in the following sentence. “The components of the powder mixture can be determined consecutively, in one experiment by titrating one component with perchloric acid in a mixture of benzene and glacial acetic acid; then the other one by resuming titration after addition of Hg(II) acetate.”

1. aminophenazone + caffeine 2. lidocaine + ephedrinium chloride 3. papaverine chloride + caffeine 4. aminophenazone + ethylmorphine chloride 5. benzocaine + phenacetin


48

212. Which of the following inorganic drugs are practically insoluble in water ?

1. BaSO4 2. Na2SO4 3. Na2HPO4 4. KI 5. MgO

213. Which of the inorganic drugs listed below give a precipitate in aqueous solution with silver nitrate under adequate circumstances?

1. ZnO 2. NaCl 3. NaH2PO4 4. NaHCO3 5. Na2SO4

214. Which of the following compounds give a positive FEHLING reaction?

1. lactose 2. mannitol 3. glycerine 4. sorbitol 5. saccharin

215. Which statements are true? 1. The partition coefficient does not depend on temperature. 2. The partition coefficient is the activity ratio of a substance in two immiscible

solvents. 3. The partition coefficient depends on the concentration of the substance. 4. In the calculation of partition coefficients, activities can be replaced by

concentrations in the case of dilute solutions. 5. The lower the partition coefficient, the more lipophilic the substance is.

216. What data are needed to calculate the proportion of the transport form of monovalent weak acids?

1. logP: (partition coefficient) 2. pKa : (ionozation constant) 3. pH : (that of the given environment) 4. c : (the total concentration of the substance) 5. Mr : (relative molar mass)


49

217. What data are needed to calculate the proportion of the protonated (receptor) form of

monovalent weak base-type drugs? 1. pH (that of the given environment) 2. c (the total concentration of the substance) 3. logP (partition coefficient) 4. Mr (relative molar mass) 5. pKa (ionization constant)

218. Which impurity tests are prescribed by Ph. Hg. VII. in the case of ethanol? 1. phosgene 2. methanol 3. peroxide 4. furfural 5. chloroform

219. Which of these general anaesthetics contain a halogen atom? 1. thiobutabarbital 2. halothane 3. isoflurane 4. metohexital 5. propanidid

220. Which of the following compounds are ketoses? 1. glucose 2. lactose 3. fructose 4. erythrose 5. mannitol

221. Which of the following drug molecules contain an aminoalcohol moiety? 1. ephedrine 2. nifedipine 3. imipramine 4. baclofen 5. amphetamine

222. Which compounds are dicarboxylic acids? 1. malic acid 2. citric acid 3. caproic acid 4. propionic acid 5. tartaric acid


50

223. Which liquids are miscible with water in any proportion?

1. Benzinum 2. Alcoholum isopropylicum 3. Glycerinum 4. Paraffinum liquidum 5. Aether

224. Which compounds are amphoteric? 1. baclofen 2. ethylmorphine 3. benzocaine 4. thymol 5. nicotinic acid

225. Which of the following terms and symbols denote types of tautomerism? 1. Z — E 2. enol — oxo 3. cis — trans 4. lactam — lactim 5. R — S

226. Which of the following compounds are enantiomers? 1. E-cinnamic acid – Z- cinnamic acid 2. R-proline – S-proline 3. L-tartaric acid – meso-tartaric acid 4. (+)-naproxen – (–)-naproxen 5. cis-cyclohexane-1,2-diol – trans-cyclohexane-1,2-diol

227. Which of the following statements are true? 1. Terc-butanol and diethyl ether are structural isomers. 2. According to the CAHN-INGOLD-PRELOG convention d-glycerin-aldehyde has

S-configuration. 3. The 1,2-diequatorial substituents of cyclohexane are in cis position. 4. Compounds having R-configuration rotate the plane of the polarized light

clockwise (to the right). 5. D-tartaric acid and meso-tartaric acid are epimers.


51

228. Which statements are true?

1. If neither sides of a double bond have identical substituents, these are ranked based

on the CAHN-INGOLD-PRELOG convention to name the Z-E isomers. 2. 3α-androstanol is the enantiomer of 3β-androsztanol. 3. Both lactam-lactim and enol-oxo tautomerism are characteristic to barbiturates

therapeutically used. 4. Each natural α-amino acid contains a chiral carbon atom. 5. The physicochemical properties of Z-E isomers are identical, they differ only in their

conformation.

229. Which isomerism or tautomerism types are possible in the case of hexobarbital? 1. enol – oxo 2. lactam – lactim 3. R – S 4. cis – trans 5. Z – E

230. Which of the following compounds are constitutional isomers? 1. methyl-p-hydroxybenzoate – methyl salicylate 2. quinine – quinidine 3. tropine – Ψ-tropine 4. acetylsalicylic acid – phenylmalonic acid 5. maleic acid – fumaric acid

231. Complete the following sentence with the correct words. A and B are ....

N

H5C2O

H5C2O

OC2H5

OC2H5

A

NH

H5C2O

H5C2O

OC2H5

OC2H5

B

1. tautomers 2. diastereomers 3. epimers 4. conformers 5. enantiomers


52

232. Which properties are characteristic of inhalation narcotics?

1. high molecular mass 2. volatility 3. high association ability 4. absence of polar functional groups 5. low lipophilicity

233. Which of the following statements are true? Chloroform:

1. is miscible with water in any proportion. 2. has a higher density than water. 3. is a flammable organic solvent. 4. can contain phosgene impurity. 5. is an intravenous narcotic drug.

234. Which statements referring to morphine are correct? 1. Its isoelectric point is in the acidic pH region. 2. Its injection solution can be stabilized by adjusting its pH to about 3 – 3.5. 3. It is an optically inactive molecule. 4. It is more polar than its semisynthetic ether derivatives. 5. Its specific identification reaction is the CALMBERG-HUSEMANN reaction.

235. Which statements are false for morphine? 1. It contains a secondary nitrogen. 2. It contains an acidic phenol functional group. 3. It is an amphoteric molecule. 4. It contains several asymmetric carbon atoms. 5. It contains a tetrahydropyrane ring.

236. Which of the following statements for morphine are correct? 1. Morphine contains a tertiary alcoholic hydroxyl and a tertiary amino group. 2. The 5 chirality centers of morphine are situated next to one another. 3. During the morphine → apomorphine rearrangement the number of asymmetry

centers decreases. 4. The aromatic ring of the molecule has a boat conformation. 5. The basic nitrogen is situated in the piperazine ring of the morphinane skeleton.


53

237. Which reactions can be applied to differentiate morphine from codeine and

ethylmorphine? 1. CALMBERG-HUSEMANN reaction. 2. By adding FeCl3 to its aqueous solution, a blue color develops. 3. Upon heating its solution with KH(IO3)2 the color turns to brown. 4. By adding phosphomolybdic acid to its aqueous solution a yellow precipitate is

formed. 5. MARQUIS reaction.

238. Choose the correct statements for semisynthetic morphine derivatives. 1. Saturation of the C7=C8 double bond increases the analgesic and antitussive

activity. 2. Ethylmorphine is the 3-ethyl ester of morphine. 3. Oxidation of the alcoholic OH to a ketone decreases the analgesic and antitussive

activity. 4. Azidomorphine has an antagonistic activity. 5. Lipophilicity decreases on etherification of the phenolic OH.

239. Which are the most important structural elements responsible for the major analgesic activity?

1. morphinane nucleus 2. planar, aromatic ring 3. levorotatory enantiomer 4. basic nitrogen 5. two carbon atoms between the basicity center and the aromatic ring

240. Choose the correct sentences. 1. The presence of a free phenolic hydroxyl group is necessary for the apomorphine

rearrangement. 2. The presence of a C7=C8 double bond is necessary for the apomorphine

rearrangement. 3. In the apomorphine rearrangement ring C of morphine becomes aromatic. 4. Apomorphine is a narcotic analgesic drug. 5. Apomorphine is more stable than morphine.

241. Which of the following functional groups can be found in fentanyl? 1. carboxylic acid amide 2. ester 3. phenolic hydroxyl 4. alcoholic hydroxyl 5. carboxylic acid


54

242. Which sentences are correct?

1. Methadone is a morphine analogue with a piperidine ring. 2. The analgesic activity of methadone derivatives equals or exceeds that of morphine. 3. Methadone contains two chiral carbon atoms. 4. Methadone can be titrated with perchloric acid in glacial acetic acid. 5. The activity of the diastereomers of methadone is significantly different.

243. Which statements are false for the minor analgesic salicylates? 1. Salicylic acid is not administered orally due to its gastric mucous membrane

irritating property. 2. Acetylsalicylic acid hydrolyses rapidly to salicylic acid in the organism. 3. The absorption of acetylsalicylic acid from the stomach is unfavourable, since it

occurs mainly in ionized form at the pH of the stomach. 4. Salicylic acid is assumed to be the active metabolite of salicylates. 5. Salicylates have three characteristic activities: analgesic, antipyretic and

antirheumatic.

244. Which compound types belong to the nonsteroidal anti-inflammatory drugs? 1. morphinane derivatives 2. anthranilic acid derivatives 3. 1,4-dihydropyridines 4. arylacetic acid derivatives 5. 1-imidazoline derivatives

245. Which of the following statements are true? Noraminophenazone sodium mesylate:

1. is synthesized from sodium methanesulfonate. 2. hydrolyses in acidic medium with the formation of sulfur trioxide. 3. contains a 3-pirazoline ring. 4. contains an asymmetrical carbon atom. 5. displays lactam-lactim tautomerism.

246. Choose the correct sentences. 1. Salicylic acid can be determined by acid-base titration. 2. Salicylic acid can be identified by the KOLBE-SCHMITT color reaction. 3. Salicylic acid gives a flesh-colored precipitate with Fe(III) ions. 4. Due to its meta-hydroxyl group salicylic acid is a stronger acid than benzoic acid. 5. The characteristic impurity of salicylic acid is phenol.


55

247. Choose the common properties of aminophenazone and noraminophenazone sodium

mesylate. 1. It readily hydrolyses both in acidic and basic media. 2. It can be oxidized. 3. It is sensitive to light. 4. It imparts a permanent yellow color to a flame. 5. Dissolved in concentrated sulfuric acid it gives a violet colour with potassium

guaiacol sulfonate.

248. Which of the following compounds are 3-pirazoline-5-one derivatives ? 1. aminophenazone 2. piroxicam 3. chlorochine phosphate 4. phenylbutazone 5. noraminophenazone sodium mesylate

249. Which of the following drug compounds contain an ester group? 1. trimethosine 2. acetylsalicylic acid 3. phenacetin 4. methyl salicylate 5. indomethacin

250. Choose the false statements relating to barbiturates. 1. Enol-oxo tautomerism is characteristic of 5,5-disubstituted barbiturates. 2. Barbituric acid displays lactam-lactim tautomerism. 3. N-substituted barbiturates do not form precipitate with mercury(II) sulfate. 4. Barbituric acid possesses four dissociable hydrogens, therefore it has an acidic

character. 5. Every 5,5-disubstituted barbiturate is optically active.

251. Choose the correct statements relating to the structure-activity relationships of barbiturates.

1. Two lipophilic substituents are necessary at position 5 for hypnotic activity. 2. Replacement of oxygen by sulfur at position 2 increases the duration of action. 3. Branching in the C5 substituents increases the duration of action. 4. There cannot be unsaturated bonds at the C5 substituents. 5. N-methyl substitution decreases the duration of action.


56

252. Which of the following structural modifications result in a decrease in the duration of

action of barbiturates? 1. Formation of sodium salt. 2. N-methyl substitution. 3. Oxo → thioxo substitution on the C2 atom. 4. Insertion of two identical substituents on the carbon atom at position 5. 5. Insertion of a phenyl group at position 5.

253. Choose the correct statements relating to the synthesis of barbiturates. 1. Maleic acid and urea are used in the simplest synthesis of barbituric acid. 2. Since the selective alkylation of barbituric acid is difficult, the C5 substituents are

inserted before ring closure. 3. During the synthesis of optically active barbiturates diastereomer mixtures are

formed. 4. Thiobarbiturates are synthesized by condensation with thiourea. 5. During the synthesis of hexobarbital the C5 cyclohexenyl group is introduced by the

alkylation of the pyridine ring.

254. Choose those barbiturates that are used as intravenous narcotics.

1.

NH

NH

O

O O

H5C2

H9C4

4.

N

NH

O

O O

CH2

CH

CHH2C

CH3C

CH5C2

CH3

2.

NH

NH

O

O S

H5C2H5C2

H3C

5.

NH

NH

O

O O

H5C2

H5C6

3.

NH

NH

O

O O

H5C2

255. Which of the following drugs give the PARRI-ZWIKKER reaction?

1. nitrazepam 2. glutethimide 3. hexobarbital 4. salicylamide 5. caffeine


57

256. Which of the following tricyclic structures form the nucleus of neuroleptic (major

tranquilizer) drugs?

1. X

R

4.

S

X

R

2.

S

N X

R

5. N

R

3. N X

R

257. Which of the following functional groups can be found in indometacin molecule?

1. ester 2. carboxylic acid 3. hydroxyl 4. carboxylic acid amide 5. nitrile

258. Choose the characteristic N10 side chain of neuroleptic phenothiazines. 1. β-phenylethyl 2. aromatic acyl 3. dimethylaminopropyl 4. aminoethyl 5. piperidinyl

259. Which statements are incorrect for phenothiazine derivatives? 1. They contain two basic nitrogen atoms. 2. They are sensitive to oxygen and light. 3. They form complexes due to their electron donor atoms. 4. They have high lipophilicity. 5. The nitrogen in the side chain can be either aliphatic or alicyclic.


58

260. Which statements are true for the structure-activity relationships of phenothiazines?

1. The steric structure has no importance in the neuroleptic activity. 2. The distance between the nitrogen atoms in the side chain and the ring must be 3

carbon atoms. 3. The increasing electron-withdrawing ability of the C2 substituent enhances the

neuroleptic activity. 4. The aliphatic or alicyclic environment of the nitrogen in the side chain has no

influence on the activity of phenothiazines. 5. Branching in the N10 side chain eliminates the neuroleptic activity.

261. Which statements are correct for the structure-activity relationships of anxiolytic 1,4-benzodiazepines?

1. The presence of an aromatic substituent at position 5 is necessary for the activity. 2. An electron-withdrawing group at position 7 decreases the activity. 3. The presence of an aromatic substituent at position 6 is essential for the activity. 4. The presence of an alkyl substituent at position 5 is necessary for the activity. 5. The insertion of a nitro group at position 7 results in antagonistic activity.

262. Choose the heterocyclic components that can be found in the structure of midazolam. 1. morpholine 2. 1,4-benzodiazepine 3. triazole 4. imidazole 5. pirazole

263. What are the main groups of anxiolytics (minor tranquilizers) based on their structure? 1. benzodiazepine derivatives 2. piperazinedione derivatives 3. barbituric acid derivatives 4. urethane derivatives 5. propanediol derivatives

264. Which statements are correct for the molecule of the given structure?

CH2 C

CH3

H

N

CH3

CH2 C CH

1.

2.

3.

4.

5.

It is a sympathomimetic phenylalkylamine.

It is an achiral molecule.

It is a selective MAO-B inhibitor antiparkinsonian drug.

It is an amphoteric molecule.

It contains an allyl group.


59

265. Which statements for neostigmine are false?

1. Neostigmine is a phenolic ester. 2. It contains a quaternary nitrogen atom. 3. It is an indirect parasympatholytic drug. 4. Neostigmine is more stable than physostigmine. 5. During its alkaline hydrolysis dimethylamine is formed.

266. Which words complete the sentence correctly? Scopine (A) and scopoline (B) are ... of each other.

O

N

CH3

H

OH

HO

N

CH3

H

O

A B

1. structural isomers 2. diastereomers 3. epimers 4. enantiomers 5. conformers

267. Choose the correct statements relating to trantheline bromide. 1. It is a tertiary ammonium salt. 2. It is an ester derivative. 3. Its acid component is xanthene-9-carboxylic acid. 4. Its alcohol component is diisopropyl-(2-hydroxyethyl)-amine. 5. It easily penetrates the blood-brain barrier.

268. Which acids are used for esterification in synthetic parasympatholytics instead of tropic acid?

1. xanthene-9-carboxylic acid 2. xanthine-9-carboxylic acid 3. carbamic acid 4. benzoic acid 5. mandelic acid

269. Which of the following statements are false? Ephedrine:

1. contains a primary amino group. 2. is a phenylalkylamine. 3. forms a violet complex with copper (II) sulfate in basic medium. 4. contains two asymmetrical carbon atoms. 5. and Ψ-ephedrine are diastereomers.


60

270. Which of the following functional groups can be found in epinephrine (adrenaline)?

1. tertiary aliphatic amine 2. phenolic hydroxyl group 3. primary aliphatic amine 4. secondary aliphatic amine 5. tertiary alcoholic hydroxyl group

271. Which of the following compounds belong to catecholamines? 1. amphetamine 2. epinephrine 3. ephedrine 4. isoprenaline 5. prenylamine

272. Which of the following groups can sympathomimetics belong to based on their chemical structure?

1. aryloxyalkanolamine derivatives 2. dihydroxyphenylalkylamines 3. phenylalkylamines 4. pyrazoline derivatives 5. indole alkaloids

273. Which of the following compounds contain a phenolic hydroxyl group? 1. atropine 2. epinephrine 3. lidocaine 4. estradiol 5. vincamine

274. Which of the following compounds do not contain a primary amino group?

1. Benzocainum 2. Ergotaminium tartaricum 3. Epinephrinum 4. Procainium chloratum 5. Sulfadimidinium

275. Which are the correct statements for oxprenolol? 1. It has a β-sympatholytic effect. 2. It contains an acetylenic bond. 3. It has an indole skeleton. 4. It contains tertiary nitrogen. 5. It contains two ether bonds.


61

276. Which are the correct statements for cocaine?

1. It is a tropine ester. 2. It is an ecgonine ester. 3. It is a benzoic acid ester. 4. It is a truxillic acid ester. 5. It is a cinnamic acid ester.

277. Which are the correct statements for lidocaine? 1. Its aqueous solution after alkalinization yields a blue colour with copper(II) sulfate. 2. It forms a diazonium salt with sodium nitrite in hydrochloric acid. 3. Eequ = Mr/2 on titration with perchloric acid in glacial acetic acid. 4. Eequ = Mr/2 on titration with perchloric acid in an acetic anhydride + glacial acetic

acid mixture. 5. It hydrolyses even in cool 2 M hydrochloric acid solution.

278. Which of the following local anaesthetics are carboxamides? 1. Lidocaine 2. Tetracaine 3. Procaine 4. Benzocaine 5. Cocaine

279. Local anaesthetics have characteristic structural elements. Choose the right statements. 1. The lipophilic aromatic and the hydrophilic amine part are always attached to an

ester bond. 2. A lipophilic (aromatic) part, an aliphatic intermedier chain and a hydrophilic

dialkylamine group can usually be found in their molecules. 3. Drugs of carboxamide type are used only as antiarrhythimics due to their high

stability. 4. The local anaesthetic effect may appear without the presence of the hydrophilic

dialkylamine group. 5. The N in the hydrophilic part is always in a heterocyclic ring.

280. Which of the following compounds are used for the synthesis of papaverine? 1. 3,4-Dimethoxyphenylacetamide 2. 3,4-Dimethoxybenzylamine 3. 3,4-Dimethoxyphenylacetic acid 4. 3,4-Dimethoxyisoquinoline 5. 3,4-Dimethoxybenzoic acid


62

281. Which statements relate to the digitalis glycosides?

1. Their basic structure can not be derived from 5β-gonane. 2. The condensed rings are annelated in the cis-trans-cis position. 3. Sugar molecules are not connected to the aglycone through a glycosidic bond at

position C3. 4. The polarity of the lanata glycosides is less than that of the corresponding purpurea

glycosides. 5. The solubility of the digitalis glycosides in water is poor, but they dissolve better in

apolar solvents.

282. Which formulae describe the structure of Amylium nitrosum official in the Pharmacopoeia?

1. H3C CH2 CH2 CH2 CH2 O N O 4. O N OH3C

H3C

H2CCH CH2

2. CHH3C

H3CCH2 ONOCH2

5. CH

H3C

H3CCH2 O N O

3. H3C CH2 CH2 CH2 CH2 O N

O

O

283. Which of the words correctly complete the following sentence?

D-Methyldopa and L-methyldopa are ... of each other. 1. diastereomers 2. enantiomers 3. epimers 4. tautomers 5. structural isomers

284. Which of these groups of compounds are Ca channel blockers? 1. 1-Imidazolines 2. 1,4-Dihydropyridines 3. 1-Amino-3-aryloxy-2-propanols 4. Diphenylalkylamines 5. 1,2-Benzothiazines


63

285. Which statements are true for the compounds with the following general structure?

NH

R1OOC COOR2

H3C CH3

R3

1. This is the general structure of the 1,4-dihydropyridine group of Ca channel blockers.

2. R1 and R2 are always the same. 3. R1

must not be the same as R2. 4. R3 is always in position 2'. 5. R3 is an electron-withdrawing substituent.

286. Which of the listed inorganic compounds are official antacid compounds in the Pharmacopoeia?

1. Aluminium hydroxydatum 2. Dinatrium hydrogenphosphoricum 3. Natrium sulfuricum 4. Activated charcoal 5. Natrium hydrogencarbonicum

287. Which of the following structural modifications enhance the anabolic effect of androgens?

1. Incorporation of cis-annelated C/D rings in the molecule. 2. Incorporation of a 1-2 double bond. 3. Incorporation of a hydroxy group at position 11β. 4. 19-Nor derivatization. 5. Incorporation of a fluoro substituent at position 9α.

288. Which statements are true for human steroid hormones? 1. Their A and B rings are always saturated. 2. They contain C and D rings with trans annelation. 3. They can be identified with the Calmberg-Husemann reaction. 4. They are substituted at position 17. 5. They contain no substitutents at position 3.

289. Which statements are true for steroids? 1. The Calmberg-Husemann reaction is used for their identification. 2. Diethyl-stilboestrol dipropionate does not contain the oestran skeleton. 3. Pregnane skeleton contains C and D rings with trans annelation. 4. Ring A of hydrocortisone contains 2 double bonds. 5. Dienoestrol has the pregnane skeleton.


64

290. Which statements are true for the structure of therapeutic corticosteroids?

1. They are substituted at positions C26 and C29. 2. The ∆4,3-keto structure is characteristic. 3. The annelation of rings B/C and C/D is trans. 4. They contain a -CONHCOOEt substituent in the β position on C17. 5. They cannot contain a substituent in the α position on C11 and C17.

291. Which transformations of prednisone lead to a stronger and more selective glucocorticoid effect?

1. Esterification of 21-OH. 2. Incorporation of 9-αF and 16-CH3 groups. 3. Substitution of 21-OH with a basic group. 4. Incorporation of 6, 9-diF and 16-OH groups. 5. Saturation of the ∆4 double bond.

292. Which of these glucocorticoids contain halogen? 1. Fluocinolone 2. Prednisolone 3. Hydrocortisone 4. Depersolone 5. Dexamethasone

293. From the structures below, which are xanthine derivatives used as drugs and official in the Pharmacopoeia?

1. HN

NH

NH

N

O

O

4. N

NH

N

N

O

O

CH3

H3C

2. HN

N

N

N

O

O

CH3

CH3

5. N

NH

NH

N

O

O

H3C

3. N

N

NH

N

O

O

H3C

CH3


65

294. Select the correct statements for the xanthine derivatives official in the Pharmacopoeia.

1. For their identification, Ph. Hg. VII prescribes the murexide test. 2. Caffeine react withs silver nitrate. 3. None of them are amphotheric molecules. 4. Caffeine can be titrated as acid in non-aqueous medium. 5. Winkler's test is based upon the difference in ring saturation.

295. Which statements refer to caffeine? 1. It is well soluble in water. 2. It is soluble in alkali. 3. It can be titrated as a base in non-aqueous medium. 4. It can be titrated as an acid in non-aqueous medium. 5. Its silver salt is a white precipitate.

296. Which statements are equally true for caffeine, theobromine and theophylline? 1. They are 3-methyl-substituted purine derivatives. 2. Their aqueous solutions are slightly acidic. 3. They are amphoteric. 4. Enol-oxo tautomerism is possible in the molecule. 5. Lactam-lactim tautomerism is possible in the molecule.

297. Which statements refer to hydrochlorothiazide? 1. It is a amin-type diuretic. 2. It is a saluretic. 3. Its hydrolysis leads to HCOOH. 4. It dissolves in alkalines with salt formation. 5. It contains ether bonds.

298. Which statements refer to the sulfonamide-type diuretics? 1. An unsubstituted -SO2NH2 group is needed for the acitivity. 2. They are compounds with strong basic character. 3. They are soluble in water. 4. Caffeine belong to this group. 5. Furosemide is an important member of this group.

299. Which types of drugs may have diuretic activity? 1. Xanthine derivatives. 2. 1,5-Pentamethylenetetrazole derivatives. 3. Pyrimidinetrione derivatives. 4. Tropane alkaloids. 5. 1,3,4-Thiadiazole derivatives.


66

300. Which statements refer to the structure of insulin?

1. It is a polypeptide hormone consisting of 16 amino acids. 2. It contains a shorter (A) and a longer (B) polypeptide chain, which are connected by

disulfide bridges. 3. It is an amphoteric molecule. 4. Its water solubility is best at its isoelectric point. 5. It exists as a monomer in aqueous solution.

301. Which functional groups can be found in aspartam (Nutrasweet)? 1. An alcoholic hydroxy group 2. A carboxamide 3. A carboxylic acid ester 4. A nitrile 5. A phenolic hydroxy group

302. Which amino acids can be found in aspartam (Nutrasweet®)? 1. Aspartic acid 2. Serine 3. Proline 4. Glutamic acid 5. Tyrosine

303. Which amino acids in the insulin chain have free functional groups (not bound in a peptide linkage) causing the acidic character of the insulin molecule?

1. Arginine 2. Glutamic acid 3. Lysine 4. Tyrosine 5. Histidine

304. Which amino acids in the insulin chains have free functional groups (not bound in a peptide linkage) causing the basic character of the insulin molecule?

1. Glutamic acid 2. Lysine 3. Arginine 4. Tyrosine 5. Phenylalanine

305. Which statements are characteristic of vitamines? 1. All of them are amine derivatives. 2. The human organism is not able to synthetize them. 3. They catalyse biochemical processes. 4. Vitamins are not soluble in water or fat. 5. Tocopherol is a member of vitamin B family.


67

306. Which statements refer to the chemical structure of vitamin A1? 1. Two double bonds can be found in its β-ionone ring. 2. The terminal functional group of the chain is -CH2-OH. 3. It has an all-trans configuration. 4. Its configuration at position 11 is cis. 5. It is a white crystalline substance.

307. Which are the correct sentences for Acidum ascorbicum? 1. The hydroxy groups of its intermediate in the synthesis pathway are protected by an

acetonide. 2. A chemoselective microbiological reduction is the key step in its synthesis. 3. It contains no asymmetric C atoms. 4. It is a five-membered lactam-type compound. 5. It is oxidized to dihydroascorbic acid during bromatometry.

308. The chemical name of Cholecalciferolum (Ph) is (+)-(5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3β-ol. Which statements are true?

1. The molecule is laevorotatory. 2. The C-5 double bond is Z, and C-7 has the E configuration. 3. The steroid skeleton is opened between C-9 and C-10. 4. There are 3 conjugated double bonds instead of ring C. 5. There is a hydrogen in the β position on C-3.

309. Which of the following statements are correct? 1. Ergocalciferol is the bioisostere of ergosterol. 2. Ergocalciferol is formed when ergosterol is irradiated with UV light. 3. The above reaction (point 2) is a ring-opening transformation of ergosterol. 4. 3 new double bonds are formed in the above reaction (point 2). 5. Cholecalciferol is the bioactive form of ergocalciferol.

310. Which are the characteristics of indomethacin? 1. The free carboxyl group is essential for its biological activity. 2. It is an amphoteric compound. 3. The indole and the benzene rings are co-planar. 4. It is soluble in water because of its carboxyl group. 5. It is an aromatic ketone derivative.

311. Which of the following antihistamines have an ethylenediamine-type structure? 1. Promethazine 2. Dimethindene 3. Diphenhydramine 4. Pimethixene (Zaditen®) 5. Chloropyramine


68

312. Which heterocycles can be found in the molecule of quinine?

N

H3CO

NHO

CH2

1.

2.

3.

4.

5.

Pyridazine

Quinoline

Quinuclidine

Pyrimidine

Pyrazine

313 Which statements are true for Dimenhydrinate, a compound of 8-chlorotheophylline

with 2-diphenylmethoxy-N,N-dimethylethylamine?

O NHH3C CH3 N

N

N

N

O

O

H3C

CH3

Cl

1. It is a cholamine-type benzhydrol derivative. 2. The drug is current under the name Peritol®. 3. 8-Chlorotheophylline increases anti-vomiting activity. 4. Diphenhydramine forms a molecular complex with 8-chlorotheophylline. 5. Theophylline can not be identified in the compound with the murexide reaction.

314. Which of the following statements are correct for invert soaps? 1. They are glycerine esters. 2. They contain quaternary nitrogen. 3. They are amphoteric molecules. 4. They contain a long alkyl or aralkyl chain. 5. They can be prepared in an inversion reaction.

315. Which dyes are of triphenylmethane type? 1. Fuchsin 2. Methylthionine Chloride 3. p-Ethoxychrysoidine 4. Acriflavinium Chloride 5. Brillant Green

316. Which are the correct statements for lactic acid? 1. Permanganate oxidation of lactic acid results in acetaldehyde. 2. Lactic acid contains two chiral centres. 3. Dilactide is a lactone formed from two molecules of lactic acid.


69

4. When lactic acid is heated, an eight-membered lactide is formed. 5. β-Hydroxypropionic acid is a structural isomer of lactic acid.

317. Which statements refer to Methenamine? 1. Its aqueous solution is slightly acidic. 2. It sublimes during a carefully performed burning test. 3. It contains two tertiary N atoms. 4. It has tetraaza-adamantane structure. 5. When its acidic solution is boiled, ammonia is liberated.

318. Which of the following compounds are fluoroquinolone derivatives? 1. Nitrofurantoin 2. Norfloxacin 3. Nalidixic acid 4. Pefloxacin 5. Metronidazole

319. Which methods can be used for the quantitative analysis of chemotherapeutic sulfonamides?

1. Nitritometry 2. Iodometry 3. Permanganometry 4. Acidimetry in aqueous medium 5. Acidimetry in non-aqueous medium

320. Which statements are correct for sulfonamides? 1. They have an amphoteric character. 2. They contain the sulfanylurea structure. 3. They are p-nitrobenzenesulfonamides. 4. They contain a primary aliphatic amino group. 5. They are competitive antagonists of PABA.

321. Which antiviral agents are derivatives of natural nucleosides transformed in the sugar moiety?

1. Idoxuridine 2. Zidovudine (Retrovir®) 3. Acyclovir (Zovirax®) 4. Amantadine (Viregyt-K®) 5. Ribavirin (Virazole®)

322. Which antiviral agents are derivatives of natural nucleosides transformed in the base? 1. Ribavirin (Virazole®) 2. Acyclovir (Zovirax®) 3. Amantadine (Viregyt-K®)


70

4. Zidovudine (Retrovir®) 5. Idoxuridine

323. Which of the statements relating to chloramphenicol are correct? 1. It contains two chirality centres. 2. It contains an aromatic cyano group. 3. Its palmitate ester is not soluble in water. 4. It has 8 enantiomers. 5. It is a geminal dihalogen derivative.

324. Which of the statements relating to penicillines are correct? 1. Penicillins contain β-lactam moiety. 2. Penicillins contain a thiazine moiety. 3. Their acidic character is due to lactam-lactim tautomerism. 4. They are a chiral molecules. 5. They are prone to degradation also in acidic and basic medium.

325. Which are the correct sentences about penicillin derivatives? 1. They contain a thiazine ring. 2. The syntheses of semisynthetic penicillin derivatives start from 6-aminopenicillanic

acid. 3. There are 3 carboxamide groups in the basic structure. 4. The basic skeleton is a dipeptide. 5. They can not be taken orally because of their acid lability.

326. Which of the statements relating to cephalosporins are correct? 1. They contain no chiral centres. 2. They contain a β-lactone ring. 3. They contain a thiazolidine ring. 4. Their stability is higher than that of penicillins. 5. They have stronger antibacterial activity as compared with penicillins.

327. Which of the statements relating to streptomycin are correct? 1. Streptomycin is an antibiotic of polypeptide type. 2. Its aglycon is streptidine. 3. The name of the sugar part is streptobiosamine. 4. Dihydrostreptomycin is formed on oxidation of the formyl group of L-streptose. 5. Streptomycins differ only in their polypeptide parts.

328. Which statements are characteristic of the tetracycline antibiotics? 1. Their skeleton is an angularly condensed tetracycle. 2. They are amphoteric. 3. There are 2 aromatic rings in the skeleton.


71

4. Their basicity centre is the N atom linked to ring A. 5. The formation of epitetracyclines does not involve a reduction of the effect.


72

329. Which of the following cytotoxic drugs are intercalating agents?

1. Chlorambucil 2. Dactinomycin 3. Tamoxifen 4. Doxorubicin 5. Cyclophosphamide


73

4. Categorizat ion Pair each of the numbers with the appropriate capital letters.

330. Pair the symbols and parameters used in UV-VIS spectrophotometry.

1. A1cm1%

A. Transmittance

2. l B. Wavelength

3. A C. Concentration of solution measured

4. ε D. Absorbance

5. λmax E. Molar absorptivity

F. Wavelength of measurement

G. Absorptivity (specific absorbance)

H. Path length

331. The Figure shows a schematic picture of a potentiometric titration system, where an

argentometric titration is carried out with potentiometric end-point detection. Pair the numbers and the parts of the system.

1

23

4

5

A. Ampere meter B. Silver electrode C. Distilled water D. Agar-agar salt bridge E. Calomel electrode F. Electrolyte solution G. Voltmeter H. Empty glass tube

332. Choose the appropriate electrodes you would use for end-point detection in the

following titration methods.

1. Combined glass electrode A. Argentometry

2.

3.

Double Pt electrode

silver-calomel electrode

B.

C.

Karl-Fischer water determination

Titration with sodium tetraphenyl-borate

4. Potassium ion-selective + calomel electrode

D. Acidimetric titration


74

333. The graph shows the titration diagram of the potentiometrically measured argentometry

of a mixture containing papaverinium chloride, theophylline and phenobarbital. Which parts of the curve refer to the listed components?

A.

B.

C.

D.

Theophylline (neutral pH)

Papaverinium chloride (on acidic pH)

Phenobarbital (at alkaline pH)

Theophylline and phenobarbital together (at neutral pH)

334. Replace the numbers by the appropriate data.

A.

B.

C.

D.

E(mV)

dE/dV

d2E/dV2

I(µA)

335. Specify the following curves.

A. Curve B. Second derivative of potentiometric titration curve C. First derivative of potentiometric titration curve D. Amperometric titration curve


75

336. Pair the connected phenomena.

1. Refractive index A. Optical activity

2. Ilkovic equation B. Critical angle

3. Atomic absorption spectrometry C. Diffusion

4. Polarimetry D. Molecular ion fragments

5. Mass spectrometry E. Hollow cathode

337. Pair the 1H NMR chemical shifts and the listed moieties.

1.

2.

3.

4.

–CH=CH–

–OCH3

CArO

H

A.

B.

C.

D.

2-4 ppm

5-7 ppm

7-8 ppm

9-11 ppm

338. Pair the types of isomerisms with the pairs of compounds.

A. ephedrine – pseudoephedrine 1. Diastereomers

B. (D)-(+)-glyceraldehyde – (L)-(-)- glyceraldehyde 2. Z-E isomers

C. fumaric acid – maleic acid 3. Constitutional isomers

D. (D)-(-)-alanine – β-alanine 4. Enantiomers

E. morphine – apomorphine

339. Pair each compound with its characteristic moiety.

1. Quaternary salt A. Cetaceum

2. Glycoside B. Lanatosidum C

3. Vax C. Macrogolum 400

4. Aldehyde hydrate D. Cetylpyridinium chloratum

5. Polyether E. Chloral hydratum

F. Bolus alba

340. Pair the solvents with the non-aqueous medium titrations.

1. nivelling A. Hhexane 2. differentiating B. Dimethylformamide 3. neutral C. Glacial acetic acid D. Methyl ethyl ketone E. Acetic anhydride F. Pyridine G. Acetone H. Methanol


76

341. Replace the numbers by the appropriate formulas to obtain the neutralizing equations in

glacial acetic acidic medium.

1 + CH3COOH = 2 + CH3COO- 3 + CH3COOH = 4 + ClO4

- 5 + CH3COOH2

+ = 2 CH3COOH

A. CH3COOH E. BH+ (protonated form of base)

B. CH3COOH2+ F. HClO4

C. CH3COO - G. ClO4-

D. B (monovalent base) H. H+

342. A four-component mixture is shaken with 10% NaOH and then extracted with 70 ml

chloroform. Pair the components with the phase they are in after the extraction. 1. Aqueous-alkaline phase A. Acetylsalicylic acid

2. Chloroform B. Ethylmorphine

C. Caffeine

D. Phenacetin

343. Choose the appropriate solvent, titrant and indicator for the determination of

hydrochlorothiazide in Hypothiazid® tablets. 1. Solvent A. Acetic acid

2. Titrant B. Thymolphthalein

3. Indicator C. Perchloric acid

D. Sodium hydroxide

E. Methanol

F. Tropeolin

G. Acetic anhydride


77

344. Pair the characteristic features and reactions with the structures.

1. Boiling with phosphoric acid gives a smell of acrolein. 2. When this cyclic ureide is boild with alkali, NH3 is realised. 3. Contains an ether bond. 4. Gives a hydrazone derivative with dinitrophenylhydrazine. 5. Boiling with alkali gives a smell of trimethylamine. 6. Heating with sodium carbonate gives a smell of pyridine.

A.

O

N

MeO

HO

Me

B.

N

NH

O O

O

Et

H

C. CH2OH

CHOH

CH2OH

D.

O

Me O

HH

H

O

E. Me

N

Me

MeHO

OCl

F.

N

COOH

345. Pair the reagents applied in the impurity tests prescribed by the Pharmacopoeia with the

ion to be detected. 1. Lead A. HgBr2

2. Iron B. Na[B(C6H5)4]

3. Nitrate C. (NH4)2(COO)2

4. Calcium D. Na2S

5. Arsenic E. KSCN

F. FeSO4

G. K2Cr2O7

346. Pair the phenomena and the impurity tests prescribed by the Pharmacopoeia.

1. Discolouration A. Heavy metal 2. Durbidity (opalescence) B. Potassium C. Sulfate D. Chloride E. Nitrate F. Nitrate + ammonia


78

347. Pair the terms and the definitions.

1.

2.

Residue on ignition

Residue on drying

A. Loss in mass due to ignition, expressed in g/g%.

3. Sulfated ash B. Residue on heating with concentrated sulfuric acid and ignition, expressed in g/g%.

C. Residue on heating and ignition, expressed in g/g%.

D. Residue on drying to constant mass at 105 °C, expressed in g/g%.

348. Pair the substances and the assay methods prescribed by the Pharmacopoeia.

1. Argentometry A. Ferrosum sulfuricum

2. Alkalimetry B. Barbitalum

3. Acidimetry (in non-aqueous solution)

C.

D.

Papaverinium chloratum

Acidum boricum

4. Bromometry E. Phenolum

5. Oxidimetry F. Triaethanolaminum

349. Pair the drugs and the identification reactions.

1. Papaverine A. Chen-Kao reaction

2. Physostigmin B. Vitali reaction

3. Ergometrine C. Coralyn reaction

4. Atropine D. Helch reaction

5. Ephedrine E. van Urk reaction

6. Pilocarpine F. Rubreserine reaction

7. Caffeine G- Marquis reaction

H. Murexide reaction

350. Pair the drugs and the identification reactions.

1. Chen-Kao reaction A. Ephedrine

2. Murexide reaction B. Caffeine

3. Marsh reaction C. Arsenic trioxide

4. Coralyn reaction D. Scopolamine

5. Thalleiochin reaction E. Papaverine

6. Vitali reaction F. Quinine


79

351. What do the following log P values mean?

1. log P= 3 A. The drug dissolves 1000 times better in water than

in organic solvents.

2. log P= 0 B. The drug dissolves 1000 times better in organic solvents than in water.

3. log P= - 3 C. The drug can be equally dissolved in water and organic solvents.

D. The drug can not be dissolved in water or organic solvents.

352. Replace x, y and z by the correct data to obtain the Henderson-Hasselbach equation.

pK XY

za = + log

A.

B.

C.

D.

E.

[H+]

[HA]

[A - ]

pH

c

353. Pair the drugs and the states of ionization.

1. Ionized at tissue pH A. Salicylic acid

2. Not ionized at tissue pH B. Papaverine

C. Ascorbic acid

D. Oestradiol

E. Chlorpromazine

F. Captopril

354. Which drugs are mainly in ionized or in non-ionized form in the lower part of the small

intestine (ca. pH 8). 1. Ionized at pH 8 A. Resorcinol

2. Non-ionized at pH 8 B. Diclofenac

C. Caffeine

D. Phenobarbital

E. Glucose

F. Benzocaine


80

355. Pair the structural elements and the drugs.

1. Quaternary nitrogen A. Pilocarpine (I)

2. Cyano group B. Selegyline (II)

3. Carbamic acid ester C. Cyclodrine (III)

4. γ-Butyrolactone D. Verapamil (IV)

5. Oxime group E. Physostigmine (V)

6. Propargyl group F. Pralidoxime (VI)

O

H H

OCH3

N

NH3C

I

C

CH3

H NCH3

CH2 C CH

II

OHO

ONH

C2H5

C2H5

III

N

H3CO

H3CO CH3

CH3

CH3

N

OCH3

OCH3IV

N

NON

O

H3C

H H3C

H

CH3

CH3

V

NN

OH

CH3

I

VI


81

356. Pair the drugs and the structural elements.

1. Primary alcohol 4. Nitrile

2. Tertiary alcohol 5. Oxime

3. Primary amine 6. Amide

A.

B.

C.

D.

N

N MeO2N

OH

I

NN

OH

Me

H

OH

NMe2

OMe

N

Me

NEt2

Me

O

H

E.

F.

NMeMeO

MeO

NC

MeMe

OMe

OMe NH2

357. Pair the names and the steroid skeletons.

1. Androstane 4. Cholestane 2. Gonane 5. Oestrane 3. Cholane 6. Pregnane

A.

B.

C.

D.

E.

F.

G.


82

358. Pair the compounds and the structural elements.

NH

NHH5C2

O

OONH

NH

O

O

CH2

C

CH2 O C NH2

O

CH2 CH2 CH3

O C

O

NH2

H3C

1. 2. 3.

N NH

NH2

5.

S

NH3C

COOHO

NH

O

NH2

4.

1. Phenobarbital A. Carbamate derivative

2. Phenytoin B. Pyrimidinetrione derivative

3. Meprobamate C. Hydantoin derivative

4. Cephalexine D. Guanidine derivative

5. Debrizoquine E. Hydrazide derivative

F. β-Lactam derivative

359. Pair the following drugs and the heterocyclic skeletons.

1. Prazosine A. Indole

2. Indomethacin B. Piperazine

3. Piroxicam C. Pyrazolidine

4. Phentanyl D. Quinazoline

5. Phenylbutazone E. 1,2-Benzthiazine

F. Piperidine

G. Furan

H. Pyridazine

I. Benzthiazole

N

N

H3CO

H3CO

NH2

N

N O

O

1


83

H3CO

N

O

Cl

COOH

CH3

2

SN

CH3

OH

NH

O

N

O O

3

N

NH5C2

O

4

NN

O

O

H3C

5

360. Pair the formulas and the heterocycles.

1.

N

N

H

2.

N

N

Me

NEt2

Cl

H

3.

N

N

N

NMe

N

N

COOH

COOHO

NH2

H2N

H

4.

N

NMe

MeMe

O

5. S

NMe

6. S

N

O

N N

OH

Me

OO

H

7.

N

NN

O

H2N

O

OH OH

HO

A. 1,2,4-Triazoles E. 1-Imidazoline

B. 1,2-Benzthiazine F. Quinazoline

C. Quinolisine G. Pteridine

D. Thioxanthene H. Quinoline


84

361. Which heterocycles are present in reserpine?

N

H3CO

HH

H3COOC

O

OCH3

H

HO OCH3

OCH3

OCH3

AB

C

D

E

N

1. Ring B A. β-Carboline

2. Rings A/B B. Quinolizidine

3. Rings C/D C. Naphthyridine

4. Rings D/E D. Pyrrole

5. Rings A/B/C E. Decahydroisoquinoline

F. Indole

362. Pair the following types of isomerism or tautomerism and the compounds (give all the

possible correct isomerism/tautomerism - compound pairs): 1. Enol – oxo A. Decaline

2. Lactam – lactim B. Phenobarbital

3. cis – trans C. Ethyl acetoacetate

4. Z – E D. Lactic acid

5. R – S E. Styrene

F. Chloral hydrate

363. Pair the compounds and the types of tautomerism.

1. Lactam-lactim tautomerism

2. Enol-oxo tautomerism

3. Ring-chain tautomerism

4. There is no possibility for tautomerism in the molecule

A.

N

N

N

NO

O

Me

Me

Me

B.

N

N

N

N

O

OHH2N

O

H

C.

HN

NHEt

O

OO

D. O

O

OHHO

CH2OH

HOH

H

E. S

N

O

N N

OH

Me

OO

H

F. O

O

OH

OHOH

CH2OH

H


85

364. Pair the molecules containing double bonds and the forms of isomerism.

1. E configuration

2. Z configuration

3. No isomerism

A.

N

Cl

Br

Me

B.

N

Br

ClMe

C. Me COOH

CH2Cl

D. S

NMe2

Cl

E. S

NMe2

ClO2N

F.

BrH2C

FH2C CH2Cl

CH2Cl

365. Pair the compounds and the listed properties.

1. CHCl3 2. CH3-CH2-O-CH2-CH3

A. Its characteristic impurity is phosgene.

B. Its density is greater than that of water.

C. Nonflammable.

D. Explosive.

E. Air oxidation causes peroxide impurity.

366. Pair the formulae and the semisynthetic morphine derivatives.

O

O

H3CO

N CH3

1.

O

HO

H3CO

N CH3

2.

O

HO

H3CO

N CH3

3.

O

N

HO

N CH3

NN 4.

O

O

H3CO

N CH3

OH

5. A. Codeine E. Dihydrocodeinone B. Azidomorphine F. Oxycodone C. Dihydrocodeine G. Malorphine D. Apomorphine


86

367. Pair the drugs and the substituents R1, R2 and R3.

O

R2

R1O

N R3

R1 R2 R3

1. Morphine A. CH3 OH CH3 2. Ethylmorphine B. H OCH3 CH3 3. Nalorphine C. CH3 OH –CH=CH–CH3 4. Codeine D. H OH –CH2–CH=CH2 E. C2H5 OH CH3 F. H OH C2H5 G. H OH CH3

368. Pair the following drugs and the heterocyclic skeletons. 1. Scopolaminium Bromide A. Isoquinoline

2. Quininium Chloride B. Imidazoline

3. Naphasolinium Chloride C. Dihydropyridine

4. Noscapinium Chloride D. Piperazine

5. Niphedipine E. Quinoline

F. Tropane

369. Pair the following drugs and the heterocyclic skeletons.

1. Phenazone A. Pyiridine

2. Phenobarbital B. Isoquinoline

3. Nitrazepam C. 3-Imidazoline

4. Papaverine D. Dibenzo[b,f]azepine

5. Nicotinic acid E. 1,4-Benzodiazepine

6. Imipramine F. Pyridazine

7. quinine G. 1,4-Benzazepam

H. 3-Pyrazoline

I. Indole

J. Quinoline

K. Pyrimidine


87

370. Pair the following compounds and the substituents!

N

N

O

R3

R2

R1

R4

1.

2.

3.

4.

Nitrazepam

Clonazepam

Oxazepam

Diazepam

R1 R2 R3 R4

A. NO2 H H H B. H H H H C. NO2 H H Cl D. NO2 C6H5 H H E. Cl H OH H F. Cl CH3 H H

371. Pair the numbered parts of the structure and the following groups.

NH

N

Cl

N

N

CH31.

2.

3.

4.

A.

B.

C.

D.

E.

Secondary amino group

Methylamino group

Amidine function

N-Methylpiperazine

N-Methylpyrazoline

372. Pair the benzodiazepine molecules and the statements.

NH

N

O

O2N

1.

N

N

OH3C

Cl

2.


88

N

N

NHCH3

Cl

O

3.

N

N

H5C2

H3CO

H3CO

OCH3

OCH3

CH3

4.

A. A 2,3-benzodiazepine derivative, synthetized by Hungarian researchers.

B. An amphoteric molecule.

C. Structurally an amidine.

D. Contains an N-substituted lactam moiety.

373. Pair the psychopharmacon classes and the drugs.

1. Neuroleptics

2. Anxiolytics

3. Antidepressants

4. Psychostimulants

CH2

C

CH2

H3C CH2 CH3CH2

O

O

C

O

C

O

NH2

NH2

A.

N

N

CH3

CH3

S

Cl

D.

N

CH3

H

B.

N

N

HO Cl

E.

HO CH2 CH NH

CH3CH3 C.

N

S NNH3C

CH3

CH3

CH3Cl

F.


89

374. Pair the numbered compounds and one of each of the compounds denoted by small

letters and capital letters. 1. Atropine a. tropine A. R-Tropic acid

2. S-HyosciaminE b. scopine B. S-Tropic acid

3. Scopolamine c. scopoline C. (±)-Tropic acid

4. Homatropine d. ekgonine D. Mandelic acid

5. Methylhomatropine e. methyltropine E. Atropic acid


90

375. Pair the structures and the drugs.

1. HO

OH

CH CH2 NH CH3

HO

4. CH3NHCH2CH

OH

HO

2. CH

CH3

CH3

HO

NHCH2CH

OH

HO

5.

CH3NHCHCH

OH CH3

3. CH2 CH NH2

CH3

A. Oxedrine (Sympethamine)

B. Amphetamine

C. Norepinephrine (Noradrenaline)

D. Ephedrine

E. Epinephrine (Adrenaline)

F. Isoprenaline

376. Pair the structures and the drugs.

H3CO

NH

O

1.

NH

O

H3C

2. N

CNHNH2O

3.

A. Piperidine

B. Pyridine

C. Piperazine

D. 1,4-Oxepine

E. Morpholine

F. Pyridazine


91

377. Pair the following drugs and the substituents.

R4NHCHCH

R2

R1

R3

R1

1. Amphetamine A. R1=H, R2=OH, R3=Me, R4=Me

2. Ephedrine B. R1=OH, R2=OH, R3=H, R4=iPr

3. Epinephrine C. R1=H, R2=H, R3=Me, R4=H

4. Isoprenaline D. R1=OH, R2=OH, R3=H, R4=Me

E. R1=H, R2=OH, R3=H, R4=Me

378. Pair the types of compounds and the muscle-relaxant drugs.

1. Guaiphenesin (Relaxil-G®) A. Pyrogallol derivatives

2. Carisoprodole B. Non-depolarizing muscle relaxants with androstene skeleton

3. Suxamethonium bromide C. Succinylcholine derivatives

4. Pipecuronium bromide D. 1,3-Propanediol derivatives

E. Glycerine ethers

379. Pair the substituents and the compounds.

R O CH2 CH

HO

CH2

HNCH3

CH3

CH

1. Propranolol A. R = p-(2-methoxyethyl)phenyl

2. Oxprenolol B. R = 4-indolyl

3. Pindolol C. R = 1-(2-allyloxyphenyl)

4. Metoprolol D. R = 2,5-dichlorophenyl

E. R = 1-naphthyl

380. Pair the following antiarrhythmic drugs and their type of action.

1. β-Receptor blockers A. Atenolol

2. Ca-channel blockers B. Quinidine

3. Non-depolarizing neuro-muscular blocking agents

C. Propaphenone

D. Verapamil

E. Lidocaine

F. Metoprolol


92

381. The numbered points of captopril bind to ACE. Pair the types of bonds and the

designated points.

NO

COOHH3C

HS1

2

3

A. Ionic D. Hydrophobic

B. H-bridge (H-bond) E. Complex-forming

C. van der Waals

382. Which types are the listed antiinflammatory drugs?

1. Phenylbutazone A. Aryl acetic acid derivatives

2. Diclofenac sodium B. Anthranilic acid derivatives

3. Naproxene C. 3,5-Pyrazolidinedione derivatives

4. Flufenamic acid D. Sulfanylureas

5. Piroxicam E. Arylpropanoic acid derivatives

F. 2H-1,2-Benzothiazines

383. Complete the formula of Betamethazone with the appropriate substituents.

4CH3

3

2HCH3

O

1

OH

A.

B.

C.

D.

E.

CH3

F

OH

C(O)-CH2-OH

C(O)-CH2-CH3

384. Pair the numbered parts of the structure and the moieties.

NN

SO2S NH CH3

O

H2N

1.

2.

3.

4.

A. Thiadiazole D. Peptide linkage

B. Sulfonamide function E. Acetyl group

C. Thiadiazoline


93

385. Pair the compounds and the substituents.

N

N

N

N

O

X

R1

R2

R3

R4

1. 2. 3. 4. 5.

Caffeine Guanine Theophilline Uric acid Theobromine

X R1 R2 R3 R4

A. O CH3 H CH3 CH3

B. NH H H H H

C. O CH3 H H CH3

D. O H OH H H

E. O CH3 H CH3 H

F. S H H H H

386. Pair the compounds and the heterorings.

NN

S NH2NO2S CH3

O

H 1.

N

NHSH2NO2S

Cl

O O

H

2.

N

N

N

N

H3C

CH3

CH3O

O

3.

ON

COOH

Cl

H2NO2S

H

4.

A. Furfural E. 1,2,4-Benzothiadiazine B. Furan F 1,3,4- Benzothiadiazine C. 1,2,4-Thiadiazole G. Xanthine D. 1,3,4-Thiadiazole H. Xanthene

387. Pair the vitamins and the international names.

1. Vitamin B2 A. Retinol 2. Vitamin A1 B. Cholecalciferol 3. Vitamin B1 C. Menadion 4. Vitamin K3 D. Thiamine 5. Vitamin D3 E. Pyridoxine F. Riboflavine G. Ergocalciferol


94

388. Pair the vitamins and the heterorings.

H

N

N

N

N

N

N

COOH

COOHO

OH

H2NH

1.

N

OH

OHHO

CH3

OO

OHHO

CH2OH

HOH

H

2. 3.

N

N NH3

N

S

CH3

OHH3C

2Cl4.

A.

B.

C.

D.

E.

F.

G.

H.

I.

Pyridine

γ-Butyrolactone

δ-Valerolactone

Thiazole

Isothiazole

Pyran

Purine

Pteridine

Pyridazine

389. Pair the numbered parts of the structure and the groups.

O

HO OH

O

HO

HO 1.

2.

3.

4.

A.

B.

C.

D.

E.

γ-Butyrolactone ring

Endiol group

1,2-Dihydroxyethyl group

δ-Pyrone ring

Cyclic ester (lactone) function

390. Pair the dyes and the dye classes.

N

SO3Na

NH2

N N N

NH2

SO3Na

HSO4

N

C2H5

C2H5

NC2H5H5C2

Cl

NH2

NH2

H2N

CH3


95

N NH2H2N

CH3Cl

N

S NNCH3

CH3

H3C

CH3 Cl

A. Diaminodiphenylmethane dyes

B. Phenazine dyes

C. Phenothiazine dyes

D. Diaminotriphenylmethane dyes

E. Azo dyes

F. Triaminotriphenylmethane dyes

G. Acridine dyes

391. Complete the formula of pefloxacine with the correct substituents.

N

OH

OO

R1R2

R3

R4

R5

R6

1. R1 A. H

2. R2 B. C2H5

3. R3 C. F

4.

5.

6.

R4

R5

R6

D. NN CH3

392. Pair the following sulfonamides and the heterocyclic skeletons.

1. Sulfamethoxazole (I) A. Pyrimidine

2. Sulfamethoxydiazine (II) B. Pyrazine

3. Sulfadimidine (III) C. Pyridazine

4. Sulfathiazole (IV) D. Piperazine

5. Sulfomethoxypyridazine (V) E. Oxazole

F. Isoxazole

G. 1,2-Oxazine

H. Thiazole

I. Isothiazole

J. 1,3-Thiazine


96

ONSO2NHH2N

CH3

I II

SO2NHH2NN

NOCH3

III

SO2NHH2NN

NCH3

CH3

S

NSO2NHH2N

IV

V

SO2NHH2NNN

OCH3

393. Pair the following sulfonamides and the substituents.

H2N SO2 NHR

1. Sulfathiazole A. –H

2. Sulfamethoxazole B. –OH

3. Sulfadimidine C. –CH3

4. Sulfacetamide D. –COCH3

5.

6.

Sulfanylamide

Sulfaguanidine E. CNH

NH2

F. S

N

G. ON

CH3

H. N

N

CH3

CH3


97

394. Pair the structures and the names of the sulfonamide derivatives listed below.

H2N SO2 NHR

R

1. S

N

A.

B.

C.

Sulfadimidine

Sulfamethoxypyridazine

Sulfathiazole

2. ON

CH3

D.

E.

F.

Sulfadicramide

Sulfamethoxazole

Sulfamethoxidiazine

3. N

N

CH3

CH3

4. N

N

OCH3

5. N

N

OCH3

395. Assign the appropriate substituents to the listed semisynthetic penicillin derivatives.

N

SNH

R

O

O

CH3

CH3

COOH

1.

2.

3.

4.

5.

Methicillin

Oxacillin

Ampicillin

Carbenicillin

Mezlocillin

A.

R =

NO

H3C

C.

R =COOH

E.

R =

Cl

Cl

B.

R =NH2

D. R =

H3CO

H3CO

F.

R =

ON

N

O

SO2CH3

NH


98

5. Relat ion analysis Your task is to analyse two sentences. The first is a statement, and the second part is an

explanation or a consequence. You have to decide whether both sentences are true or not, and whether any logical

connection exists between them or not.

There are five possibilities (A- E), but only one is correct: A. Both the statement and the explanation or consequence are true, and a

causal relation exists between them. B. Both the statement and the explanation or consequence are true, but there is

no logical relation between them. C. The statement is true, but the explanation or consequence is false. D. The statement is false, but the explanation or consequence is true. E. Both the statement and the explanation or consequence are false.

396. The primary condition for the validity of the Beer-Lambert law is that all the substance

must exist in the same molecular state at different dilutions. The reason is that a deviation is observed from the linear absorbance - concentration relation as a result of association or dissociation processes.

397. In the IR spectra of organic compounds, the absorption wavenumbers corresponding to

the vibrations of C-H, N-H and O-H are high. The reason is that the atomic mass of hydrogen is small compared to those of the other atoms.

398. The Pharmacopoeia does not prescribe light absorption measurement for identification.

The reason is that the value of absorptivity is dependent on the solvent and the wavelength.

399. A two-component mixture having overlapping UV spectra can be determined at two

wavelengths. The reason is that the absorbance measured is the sum of the absorbances of the two components.

400. In the UV spectrum of a compound containing a phenolic hydroxy group, hypsochromic

and hypochromic shifts occur after alkalinization. This is why differential spectrophotometry can be applied with adjusted pH in the case of multicomponent mixtures containing a phenolic compound.

401. In spectrophotometry used for quantitative drug analysis, background correction

methods are often used. The reason is that the absorbance of other components may disturb the measurement.

402. The three-point correction or baseline method is a type of background correction method

often used in electronspectroscopy. The reason is that in the baseline method absorbance must be determined at three absorbance maxima.


99

403. The extension of conjugation in a molecule generally results in a hypsochromic shift of

the electronic (UV-VIS) spectrum. The reason is that a compound containing a more extended chromophore is excited by lower energy.

404. In an electrophilic substitution, diazotized aromatic amines can be coupled with phenols

and aromatic amines to give azo compounds, which are coloured. The reason is that their electronic systems are conjugated.

405. Extension of the chromophoric systems of organic pharmaceuticals, i.e. an increase in

the number of conjugated π-electrons (e.g. as a consequence of different reactions), will produce coloured compounds. The reason is that the conjugated π-electrons can be excited by electromagnetic radiation of lower energy than for isolated π-electrons.

406. The sensitivity of 13C-NMR spectroscopy is 1% of the sensitivity of 1H-NMR

spectroscopy. The reason is that the occurrence of the isotope 13C is only 1.1%. 407. The signal of the methyl group in the 1H-NMR spectrum of ethanol is a triplet. The

reason is that the signal splits into three according to the n+1 rule due to the neighbouring methylene group.

408. D- and L-phenylalanine can be distinguished by their optical rotations. The reason is that

the physical and chemical characteristics of diastereomers are different. 409. Specific rotation is a characteristic of optically active compounds. The reason is that

achiral compounds do not rotate the plane of a polarized light beam. 410. In an Abbe refractometer, the refractive index of a colourless substance can be measured

by using white light. The reason is that the refractive index does not depend on the wavelength in the visible region.

411. In potentiometry, electrodes of the second kind are used as reference electrodes (e.g. the

calomel electrode). The reason is that their potential is in a logarithmic relation with the activity of the substance being determined.

412. In the argentometric - potentiometric determination of chloride ion, the reference

electrode is separated from the sensing electrode and from the bulk of the solution. The reason is that the conductance is maintained with an agar-agar salt bridge.

413. The end-point of an argentometric titration can not be indicated potentiometrically. The

reason is that the silver electrode is a reference electrode which has a constant potential during an argentometric titration.

414. In instrumental pH measurements, a combined glass electrode can be used. The reason is

that in direct potentiometry there is no need for a reference electrode. 415. The calomel electrode is an electrode of the first kind. This is why it can be used as a

sensing electrode in potentiometry.


100

416. In a thin-layer chromatographic process, the larger the elution strength of the solvent is,

the higher is the Rf value. The reason is that the time spent by the substance in the solvent system increases with the elution ability of the solvent.

417. In thin-layer chromatography, well-dissociating acids can be separated by using acidic

eluents. The reason is that their affinity for the sorbent is stronger in such circumstances. 418. In gas chromatographic examinations, the retention time can be used for the

identification of the components. The reason is that the retention time is independent of the temperature of the separation column.

419. A polar stationary phase is used for the separation of the isomers of butanol by gas

chromatography. The reason is that polar compounds can be separated successfully on polar stationary phases.

420. The retention times of methyl ethyl ether (Mr = 60) and n-propanol (Mr = 60) are equal

on any stationary phase in gas chromatography. The reason is that compounds with equal molecular masses are equally volatile.

421. Isomers of aliphatic hydrocarbons can be separated most successfully by gas

chromatography on apolar stationary phases. The reason is that on apolar stationary phases (these) compounds are eluted in the sequence of their increasing boiling points.

422. In high-performance liquid chromatography for the characterization of retention

behaviour, the capacity rate (k') is used. The reason is that separation is based solely on distribution.

423. Aliphatic alcohol homologues can be well separated by normal-phase high-performance

liquid chromatography. The reason is that the adsorbent is sensitive to changes of the number in carbon atoms in molecules.

424. In high-performance liquid chromatography, the eluent is a mixture of water and a polar

solvent when the sorbent is silica. The reason is that silica is a reasonably good adsorbent of polar compounds.

425. In high-performance liquid chromatography, reversed-phase columns (C18) are often

used. The reason is that the solvent-water ratio greatly influences the selectivity of the column.

426. According to the Pharmacopoeia, lead and iron test solutions are used in the tests of

heavy metals. The reason is that, under the given conditions, only lead and iron contamination can be detected as heavy metal impurities.

427. In limit tests changing amounts of the sample under examination are used in each case.

The reason is that the changes observed in the sample and the test solutions must be equally strong.

428. In the limit tests official in the Pharmacopoeia, always 1 ml of test solution is used. The

reason is that this amount contains the allowed impurity content of each official material.


101

429. In the test of arsenic impurity, the arsenic must be reduced to oxidation state +3. The

reason is that it can be detected with HgBr2 paper after conversion into hydrogen arsenide.

430. In a limit test, the Pharmacopoeia prescribes a potassium thiocyanate reagent for the

detection of Fe(III) ions. In this examination, Fe(II) and Fe(III) ions give red precipitates with this reagent.

431. In the limit test for nitrate impurity, any ammonium contamination is also detected. The

reason is that the ammonium ion is transformed to nitrate as a result of oxidation by the concentrated sulfuric acid reagent.

432. Benzaldehyde impurity in Acidum benzoicum must be detected with fuchsin and

sulfurous acid. The reason is that benzaldehyde is a characteristic impurity of benzoic acid.

433. In a glacial acetic acid medium, the acidity of weak organic acids is increased. This is

the reason why the direct titration of bases is disturbed by the presence of weak organic acids.

434. In a non-aqueous medium, the determination of bases present in the form of

hydrochloride salts is possible only after extraction of the base from alkaline solution with chloroform. The reason is that hydrochloric acid is a medium-strong acid in non-aqueous medium.

435. The free salicylic acid impurity in acetylsalicylic acid can not be detected through its

complex with FeCl3. The reason is that acetylsalicylic acid readily hydrolyses to salicylic acid on standing in aqueous solution.

436. For the separation of hexachlorophene from its mixture with salicylic acid, aqueous

sodium carbonate solution is used. The reason is that the phenolic hexachlorophene can be selectively extracted from the solution in this way.

437. The bismuth and magnesium contents of Pulvis neutracidus (FoNo) can be assayed

complexometrically in the ignited sample without previous separation. The reason is that magnesium forms a complex with sodium edetate only in acidic solution, and bismuth forms a complex with sodium edetate only in alkaline solution.

438. The identification of phenacetin in pulvis analgeticus (Coffeinum, Phenacetinum and

Aminophenazonum) is performed by the addition of 25% nitric acid instead of concentrated nitric acid, to increase the selectivity of identification. The reason is that the disturbing effect of aminophenazone can be eliminated in this way.

439. The lidocaine and caffeine content of Suppositorium antiemeticum can be determined by

titration in non-aqueous medium. The reason is that in glacial acetic acid caffeine is sufficiently basic to be determined.

440. Pharmaceuticals containing covalently bound halogen are generally apolar, water-

insoluble compounds. They do not yield silver halides with silver ion.


102

441. According to the Cahn-Ingold-Prelog convention, a bromine substituent receives a lower

number than a chlorine substituent. The reason is that they follow each other in the ABC in this sequence.

442. Meso-tartaric acid is inactive optically. The reason is that it contains no chiral centre. 443. The Pharmacopoeia prescribes alcohol dilution in v/v%. The reason is that when alcohol

is mixed with water, a volume contraction occurs. 444. The factor of a glacial acetic acid — perchloric acid titrant increases with temperature.

The reason is that its real concentration decreases with temperature. 445. Lactose does not give a positive Fehling reaction. The reason is that it contains galactose

and glucose. 446. Fructose and glucose give positive Fehling reactions. The reason is that there is no

significant difference in reactivity of structural isomers. 447. Ionization and lipophility of drugs greatly influence their absorption. The reason is that

only hydrophilic particles can pass through cell membranes unhindered. 448. To characterize lipophilicity, the octanol/water distribution ratio is used. The reason is

that octanol can not be mixed with water. 449. The octanol/water distribution ratio measures the lipophilicity of drugs. The reason is

that this solvent system is a good model of the biological distribution (penetration) of a drug.

450. The distribution ratio of molecules that can be ionized is pH- dependent. The reason is

that in aqueous solution ionization occurs, which is dependent on the pH and pKa values.

451. The real distribution ratio is a pH-independent constant. The reason is that this constant

refers to the concentration ratio of the non-ionized particle in the organic and water phases.

452. The absorption of drugs of weak acid type is advantageous at the gastric pH. The reason

is that they are then present mostly in non-ionized (transport) form. 453. The absorption of drugs is not influenced by ionization. The reason is that absorption is

basically controlled by lipophility. 454. 50% a base with pKa = 7.4 is protonated form at the tissue pH. The reason is that

ionization is solely dependent on the pKa value. 455. Diethyl ether should be stored in completely filled, well-stoppered containers, protected

from light. The reason is that a peroxide is readily formed in diethyl ether on the action of the oxygen of the air and light.


103

456. Diethyl ether should not be stored in metal containers. The reason is that it may contain

explosive peroxide impurities. 457. Peroxides are dangerous impurities in diethyl ether. The reason is that the hydrolysis of

peroxides results in poisonous polymeric substances. 458. Phosgene is a dangerous impurity in chloroform. The reason is that moisture reacts with

phosgene to form hydrogen chloride, which causes pneumonia. 459. Morphine can be extracted into organic solvents from alkaline medium by means of the

usual alkaloid extraction methods. The reason is that morphine is a tertiary nitrogen-containing base.

460. Morphine is an amphoteric substance. The reason is that morphine contains alcoholic

hydroxy groups. 461. Codeine is less polar than morphine. The reason is that codeine contains alcoholic

hydroxy groups. 462. Morphine and codeine can be distinguished with the Marquis reaction. The reason is that

morphine and codeine differ in a single ether- bonded methyl group. 463. The activities of the major analgesics are influenced by both the lipophilicity and the

steric structure. The reason is that the lipophilicity provides access to the central nervous system, while the appropriate steric situation of the connected groups is needed for binding to the receptor.

464. Salicylic acid is a weaker acid than benzoic acid. The reason is that the acidity is

decreased by the ortho-hydroxy group, which forms a hydrogen-bond. 465. Salicylic acid is a weaker acid than its structural isomers such as m-OH-benzoic acid and

p-OH-benzoic acid. The reason is that an intramolecular hydrogen-bond is formed between its -OH and -COOH groups in the ortho position.

466. The quantitative determination of phenazone is performed bromatometrically. The

reason is that the addition of bromine to the double bond of phenazone takes place quantitatively.

467. Phenylbutazone has an acidic character. The reason is that the two carbonyl groups on

the skeleton weaken the binding of the hydrogen at position 4. 468. The more lipophilic a barbiturate molecule is, the stronger is its sedatohypnotic activity.

The reason is that the activity is in a linear relation with the lipophilicity. 469. Both hydrogens on C-5 in therapeutically usable barbiturates must be substituted. The

reason is that this increases the proportion of the non-ionic transport form in the tissues at physiological pH.


104

470. The Parri-Zwicker reaction is characteristic of, but is not selective for barbiturates. The

reason is that some xanthine and sulfonamide derivatives also give a positive reaction. 471. The quantitative determination of barbiturates containing an unsaturated moiety is

performed bromatometrically. The reason is that the substitution of bromine is a quantitative process.

472. In the argentometric determination of phenobarbital, no indicator is prescribed by the

Pharmacopoeia. The reason is that the end-point is detected via the beginning of precipitation of the disilver salt.

473. Phenobarbital is optically active. The reason is that it contains two different substituents

at position 5. 474. The oxidizability of phenothiazines permits a self-indicating cerimetric titration. The

reason is that in the acidic assay medium a gradually darkening red colour is produced, which disappears at the end-point.

475. During the hydrolysis of meprobamate, CO2 and ammonia are generated, as in the case

of urethane. The reason is that they are ester derivatives of carbamic acid. 476. When boiled with acid, the 1,4-benzodiazepines decompose to benzophenone and

glycine derivatives. The reason is that their amide moiety is sensitive to hydrolysis. 477. 1,4-Benzodiazepine type anxiolytics have a nitro group at position 7. The reason is that

the presence of an electron-withdrawing group at position 7 is one of the conditions of the anxiolytic effect.

478. Glutamic acid can not take part in biochemical transamination. The reason is that it is an

amide derivative. 479. In overdosages with parasympathomimetic alkylphosphate, the toxic effects can not be

influenced. The reason is that alkylphosphates are bound covalently in the body. 480. Atropine does not exhibit optical activity. The reason is that it does not contain an

asymmetric carbon atom. 481. The appearance of a purple-red colour in the Vitali reaction obviously refers to the

presence of atropine. The essence of the Vitali reaction is the nitration of a tropic acid moiety, after which the action of an alkali metal hydroxide yields a coloured compound.

482. Both atropine and cocaine give a positive Vitali reaction. The reason is that both

compounds contain the tropane skeleton. 483. Tropeins containing a quaternary N atom have no effect on the central nervous system.

The reason is that, due to their poor lipophylicity, they do not penetrate to the CNS. 484. Ephedrine hydrochloride quickly becomes coloured on standing in the air. The reason is

that it contains oxidizable phenolic hydroxy groups.


105

485. The addition of Cu2⊕ to an alkaline solution of ephedrine yields a reddish-violet colour

which can be extracted into butanol. The reason is that this is promoted by H-bond formation between the phenolic groups and butanol.

486. The Chen-Kao reaction can be used for the detection of ephedrine traces in

amphetamine. The reason is that ephedrine, as an amino alcohol, produces a coloration in this reaction, while amphetamine does not react.

487. The ergot alkaloids used in therapy are derivatives of D-isolysergic acid. The lysergic

acid derivatives can therefore be regarded as their enantiomers. 488. Benzocaine can be measured by bromatometry. The reason is that a tribromine

derivative arises during the reaction. 489. Benzocaine and lidocaine can be distinguished by their azo dyes. The reason is that

lidocaine does not contain a tertiary amino group. 490. When a solution of cocaine in concentrated sulfuric acid is heated and then diluted with

water after cooling, colourless crystals precipitate from the solution. The reason is that the hydrolysis of cocaine leads to tropic acid, which is poorly soluble in water.

491. The metabolism of lidocaine involves N-desalkylation. The reason is that the amide

group is sensitive to hydrolytic degradation. 492. Benzocaine is diazotized by reaction with nitrite, and then forms a coloured azo dye

with 2-naphthol. The reason is that benzocaine contains an ethyl group. 493. In the papaverine identification test, the coralyn reaction, a yellowish-green, fluorescent

compound is formed. The reason is that the isoquinoline moiety, because of its electronic structure, is an acid-base indicator.

494. The nitric esters of polyalcohols are explosive compounds. The reason is that they

contain easily cleavable carbon-nitrogen covalent bonds. 495. Niphedipine is sensitive to light. The reason is that it undergoes degradation with

intramolecular disproportionation on exposure to light. 496. Fenofibrate, which acts against atherosclerosis, is a prodrug. The reason is that its active

metabolite fenofibroic acid occurs in the body. 497. The natural estrogens form red azo dyes with diazotized sulfanilic acid in alkaline

medium. The reason is that they are sterane derivatives. 498. Esterification of the 3-phenolic and/or 17-alcoholic hydroxy groups of natural estrogens

leads to long-lasting agents arise. Natural estrogens contain the pregnane skeleton. 499. Ethynylestradiol is an orally applicable estrogen. The reason is that its 17-OH group is

protected from rapid oxidation by the introduction of an ethyl group in the 17α-position.


106

500. Testosterone can not be administered orally. The reason is that it contains the androstane

skeleton. 501. Testosterone propionate is applied in injectional preparations. This derivative is better

soluble in water than testosterone itself. 502. Norandrosterolone phenylpropionate (the active agent of Nerobolil® oily injection) is an

anabolic drug. The reason is that its 17-hydroxy group is esterified. 503. Mazipredone hydrochloride is a water-soluble glucocorticoid. The reason is that its N-

methylpiperazinyl group permits salt formation. 504. Hydrocortisone is a steroid drug with the pregnane skeleton. The reason is that the

anellation of rings A/B is cis, while the anellations of rings B/C and C/D are trans. 505. A sensitive reaction of corticosteroids is the formation of red formazans with colourless

tetrazolium salts in alkaline medium. The reason is that their 17-side-chain has strong oxidative properties.

506. The corticosteroids give a positive Fehling reaction. The reason is that they have

reducing properties due to their hydroxyacetone side-chain. 507. The corticosteroids have reducing properties. The reason is that they are ∆4-3-keto-

steroids. 508. In the therapy of certain kinds of hyperlipidaemias, ion-exchange resins containing basic

ammonium groups are applied. The reason is that, when administered orally, they bind bile acids, in this way reducing the cholesterine production of the liver.

509. The xanthine derivatives official in the Pharmacopoeia can not be distinguished from

each other with the murexide reaction. The reason is that all three react to yield a crimson-red salt of purpuric acid.

510. Caffeine forms a white, jelly-like precipitate with sodium hydroxide. The reason is that

contains an acidic hydrogen. 511. The thiazide-type diuretics are called "saluretics". The reason is that they excrete a

significant quantities of HCO3 and Na⊕ in the urine. 512. Alkalinization of the urine is a characteristic effect of carboanhydrase-blocking

diuretics. The reason is that they excrete significant quantities of HCO3 and Na⊕ in the urine.

513. Sorbitol does not react in the Fehling test. The reason is that it is a polyhydroxy

compound containing six carbon atoms. 514. One of the possibilities for the production of insulin preparations with prolonged action

is an increase of the zinc content. The reason is that the bonding of zinc ions shifts the isoelectric point of insulin to the neutral zone, and its dissolution and penetration into the blood circulation are therefore slower.


107

515. Homogeneous insulin preparations are called "monocomponent" (MC) insulins. The

reason is that, apart from insulin, they do not contain other immunogenic peptides (e.g. proinsulin, C-peptide, etc.).

516. Vitamins D are sealed in brown vials under vacuum. The reason is that they are sensitive

to light and air. 517. Tocopherol derivatives give a colour reaction in the usual phenol-iron(III) complex

formation. The reason is that the methyl groups adjacent to the phenolic hydroxy group have no effect on it.

518. Thiamine is a hydophilic vitamin. The reason is that it contains a quaternary nitrogen. 519. It is a specific reaction of thiamine that in alkaline medium, in the presence of an

oxidizing agent, a vivid-blue fluorescence appears. The reason is that the aromatic primary amino group of the pyrimidine ring and C-2 of the thiazole ring react, with ring closure.

520. The structure of vitamin B12 is very close to that of the porphyrins. The reason is that

vitamin B12 contains a cobalt(III) atom. 521. The configurations of C-4 and C-5 of ascorbic acid are the same as in L-gulonic acid.

The reason is that, after enolization of the keto groups on C-2 and C-3, these atoms become chiral.

522. The ascorbic acid identity tests are based on its endiol moiety. The reason is that there is

no alcoholic hydroxy group in the structure. 523. The pyran ring of flavonoids opens easily. The reason is that this results in a flavonoid-

calcone equilibrium. 524. Prostaglandins can be classified as alicyclic compounds. The reason is that their basic

skeleton, consisting of 20 carbon atoms, contains a cyclopentane ring. 525. The pyrazolidinedione derivative-containing pharmaceutical preparations are stable

during storage. The reason is that the two acid amide bonds stabilize the molecule. 526. In the molecule of phenylbutazone, lactam-lactim tautomerism is possible. The reason is

that the 1,2,4-trisubstituted pyrazolidine-3,5-diones are C-H acidic compounds. 527. Indomethacin is an optically active compound. The reason is that the anti-inflammatory

agents of α-arylpropionic acid type contain at least one asymmetry centre. 528. The acidic character of the OH group of benzhydrol is stronger than that of phenol. The

reason is the stronger electron-attracting effect of the two aromatic rings. 529. Benzenesulfone-chloroamide sodium is a good disinfectant. The reason is that, during its

application, benzenesulfonamide is released.


108

530. Quinine has theoretically 24 = 16 diastereomers. The reason is that quinine contains four

chiral centres. 531. Addition of bromine to quinine or quinidine takes place readily. The reason is that they

contain a vinyl group. 532. Cinchonidine does not give the thalleiochin reaction. The reason is that one criterion of a

positive thalleiochin reaction among the Quina alkaloids is that the quinoline ring must contain an OH or OCH3 group at position 6'.

533. An aqueous solution of quinine chloride fluoresces a vivid-blue colour. The reason is the

presence of an oxygen-containing functional group at position 6' on the quinoline ring. 534. The aromatic primary amino group of sulfonamides is essential for their activity. The

reason is that the basicity strength determines the half-life of the drug. 535. Chloramphenicol has cis and trans isomers. The reason is that it contains two chiral

centres. 536. Chloramphenicol has two enantiomers. The reason is that it contains two chiral centres. 537. The sodium salt of chloramphenicol hydrogensuccinate is applied for injectional

preparations. The reason is that chloramphenicol is slightly soluble in water. 538. All effective compounds among the fluoroquinolines contain the 4-pyridone-3-

carboxylic acid moiety. The reason is that the introduction of fluorine in different positions in the molecules increases their effects.

539. 6-Aminopenicillanic acid (6-APA) is the key intermediate of penicillin production. The

reason is that it is pharmacologically more effective than the biosynthetic derivatives. 540. Methicillin is resistant to penicillinase. The reason is that the aromatic ring connected to

the exocyclic carboxamide contains two methoxy groups in the ortho position, which sterically inhibits hydrolysis of the β-lactam moiety.

541. The semisynthetic penicillin derivatives are more advantageous than the biosynthetic

products. The reason is that the introduction of an appropriate substituent can yield enzyme-resistant and acid-resistant products.

542. The penicillins are stable against acids. The reason is that the β-lactam ring does not

open in acidic media. 543. In acetic acid media, the decomposition of cephalosporins is fast. The reason is that they

contain more than 2 chiral centres. 544. Tetracyclines are yellow. The reason is that they contain conjugated double bonds. 545. Anticancer complexes of platinum do not interfere with the biological functions of

DNA. The reason is that they bind mainly to the purine bases in the DNA chain.


109

546. Nitrogen mustard type anticancer alkylating agents react with the electrophilic groups of

biomolecules. The reason is that their mercapto groups bind the metal ions necessary for the activity of enzymes.


110

6. Answer Key

1. D 2. C 3. D 4. D 5. B 6. A 7. B 8. D 9. E 10. D 11. E 12. A 13. C 14. A 15. D 16. B 17. E 18. D 19. D 20. D 21. B 22. E 23. A 24. E 25. E 26. A 27. B 28. B 29. B 30. C 31. A 32. E 33. D 34. B 35. B 36. D 37. B 38. B 39. D 40. A 41. E 42. B

43. E 44. C 45. D 46. D 47. A 48. C 49. E 50. D 51. D 52. B 53. D 54. B 55. A 56. A 57. A 58. C 59. C 60. C 61. B 62. B 63. D 64. D 65. B 66. B 67. E 68. B 69. B 70. D 71. D 72. B 73. E 74. C 75. C 76. C 77. B 78. B 79. A 80. C 81. C 82. B 83. A 84. C

85. C 86. E 87. B 88. B 89. C 90. C 91. D 92. C 93. E 94. B 95. D 96. D 97. B 98. D 99. D 100. D 101. D 102. B 103. B 104. E 105. D 106. A 107. A 108. B 109. C 110. B 111. E 112. B 113. B 114. C 115. A 116. D 117. C 118. E 119. C 120. B 121. D 122. C 123. A 124. C 125. C 126. E

127. A 128. D 129. B 130. E 131. D 132. E 133. C 134. E 135. A 136. D 137. D 138. C 139. D 140. C 141. D 142. E 143. A 144. B 145. C 146. D 147. A 148. D 149. C 150. E 151. D 152. B 153. D 154. B 155. C 156. C 157. B 158. B 159. D 160. C 161. B 162. D 163. E 164. A 165. A

166. D 167. C 168. E 169. C 170. E 171. E 172. D

173. E 174. D 175. E 176. C 177. E 178. E 179. E

180. C 181. B 182. D 183. C 184. E 185. E 186. C

187. D 188. E 189. E 190. A 191. E 192. B 193. D


111

194. C 195. E 196. A 197. B 198. A 199. C 200. E 201. A 202. C 203. D 204. E 205. A 206. E 207. E 208. E 209. B 210. D 211. E 212. C 213. D

214. A 215. E 216. D 217. C 218. E 219. D 220. B 221. A 222. C 223. D 224. C 225. E 226. E 227. C 228. A 229. E 230. D 231. A 232. E 233. E

234. E 235. C 236. D 237. D 238. A 239. E 240. D 241. A 242. E 243. B 244. E 245. B 246. C 247. D 248. C 249. E 250. C 251. C 252. D 253. E

254. E 255. D 256. E 257. E 258. B 259. A 260. D 261. A 262. E 263. C 264. B 265. B 266. A 267. D 268. C 269. A 270. E 271. E 272. D 273. E

274. D 275. C 276. D 277. A 278. A 279. E 280. B 281. E 282. E 283. D 284. E 285. C 286. C 287. E

288. E 289. D 290. D 291. E 292. C 293. D 294. A 295. B 296. A 297. E 298. C 299. C 300. D 301. D

302. A 303. E 304. D 305. D 306. D 307. A 308. D 309. D 310. A 311. C 312. D 313. A 314. E 315. C

316. C 317. E 318. E 319. C 320. C 321. D 322. C 323. C 324. C 325. E 326. E 327. D 328. E 329. E

330. 1. G 330. 2. H 330. 3. D 330. 4. E 330. 5. F 331. 1. G 331. 2. B 331. 3. E 331. 4. D 331. 5. F 332. 1. D 332. 2. B 332. 3. A 332. 4. C 333. 1. B 333. 2. A 333. 3. C 334. 1. C 334. 2. A 334. 3. B

335. 1. B 335. 2. A 335. 3. C 336. 1. B 336. 2. C 336. 3. E 336. 4. A 336. 5. D 337. 1. B 337. 2. A 337. 3. D 337. 4. C 338. 1. A 338. 2. C 338. 3. D 338. 4. B 339. 1. D 339. 2. B 339. 3. A 339. 4. E

339. 5. C 340. 1. B, C, E, F 340. 2. D, G 340. 3. A, H 341. 1. D 341. 2. E 341. 3. F 341. 4. B 341. 5. C 342. 1. A 342. 2. B, C, D 343. 1. E 343. 2. D 343. 3. B 344. 1. C 344. 2. B 344. 3. A 344. 4. D 344. 5. E 344. 6. F

345. 1. D 345. 2. E 345. 3. F 345. 4. C 345. 5. A 346. 1. A, E, F 346. 2. B, C, D 347. 1. C 347. 2. D 347. 3. B 348. 1. B 348. 2. D 348. 3. C 348. 4. F 348. 5. A 349. 1. C 349. 2. F 349. 3. E 349. 4. B 349. 5. A


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349. 6. D 349. 7. H 350. 1. A 350. 2. B 350. 3. C 350. 4. E 350. 5. F 350. 6. D 351. 1. B 351. 2. C 351. 3. A 352. X. D 352. Y. B 352. Z. C 353. 1. A, C, E, F 353. 2. B, D 354. 1. B, D 354. 2. A, C, E, F 355. 1. F 355. 2. D 355. 3. E 355. 4. A 355. 5. F 355. 6. B 356. 1. A 356. 2. C 356. 3. F 356. 4. E 356. 5. B 356. 6. D 357. 1. C 357. 2. A 357. 3. E 357. 4. G 357. 5. B 357. 6. D 358. 1. B 358. 2. C 358. 3. A 358. 4. F 358. 5. D 359. 1. B, G 359. 2. A 359. 3. E 359. 4. F 359. 5. C 360. 1. E 360. 2. H 360. 3. G 360. 4. C, F 360. 5. D 360. 6. B

360. 7. A 361. 1. D 361. 2. F 361. 3. B 361. 4. E 361. 5. A 362. 1. C 362. 2. B 362. 3. A 362. 4. E 362. 5. D 363. 1. C, B 363. 2. E, D 363. 3. F 363. 4. A 364. 1. F 364. 2. B, C, D, E 364. 3. A 365. 1. A, B, C 365. 2. D, E 366. 1. E 366. 2. C 366. 3. A 366. 4. B 366. 5. F 367. 1. G 367. 2. E 367. 3. D 367. 4. A 368. 1. F 368. 2. E 368. 3. B 368. 4. A 368. 5. C 369. 1. H 369. 2. K 369. 3. E 369. 4. B 369. 5. A 369. 6. D 369. 7. J 370. 1. A 370. 2. C 370. 3. E 370. 4. F 371. 1. B 371. 2. D 371. 3. C 371. 4. A 372. 1. A 372. 2. D 372. 3. C

372. 4. A 373. 1. D 373. 2. A 373. 3. B 373. 4. E 374. 1. a, C 374. 2. a, B 374. 3. b, B 374. 4. a, D 374. 5. e, D 375. 1. E 375. 2. F 375. 3. B 375. 4. A 375. 5. D 376. 1. A 376. 2. E 376. 3. B 377. 1. C 377. 2. A 377. 3. D 377. 4. B 378. 1. E 378. 2. D 378. 3. C 378. 4. B 379. 1. E 379. 2. C 379. 3. B 379. 4. A 380. 1. A, F 380. 2. D 380. 3. B, C, E 381. 1. E 381. 2. B 381. 3. A 382. 1. C 382. 2. A 382. 3. E 382. 4. B 382. 5. F 383. 1. B 383. 2. A 383. 3. D 383. 4. C 384. 1. B 384. 2. A 384. 3. D 384. 4. E 385. 1. A 385. 2. B 385. 3. C

385. 4. D 385. 5. E 386. 1. C 386. 2. E 386. 3. H 386. 4. B 387. 1. F 387. 2. A 387. 3. D 387. 4. C 387. 5. B 388. 1. H 388. 2. A 388. 3. B 388. 4. D 389. 1. A 389. 2. E 389. 3. B 389. 4. C 390. 1. E 390. 2. F 390. 3. D 390. 4. G 390. 5. C 391. 1. B 391. 2. A 391. 3. D 391. 4. C 391. 5. A 391. 6. A 392. 1. F 392. 2. A 392. 3. A 392. 4. H 392. 5. C 393. 1. F 393. 2. G 393. 3. H 393. 4. D 393. 5. A 393. 6. E 394. 1. C 394. 2. E 394. 3. A 394. 4. F 394. 5. B 395. 1. D 395. 2. A 395. 3. B 395. 4. C 395. 5. F

396. A 397. A 398. D 399. A

400. D 401. A 402. C 403. D

404. A 405. D 406. B 407. A

408. B 409. B 410. C 411. C


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412. B 413. E 414. C 415. E 416. A 417. C 418. C 419. A 420. E 421. A 422. C 423. E 424. D 425. B 426. C 427. C 428. C 429. A 430. C 431. E 432. B 433. E 434. D 435. D 436. C 437. C 438. C 439. C 440. A 441. B 442. C 443. A 444. D 445. D 446. C 447. C 448. B 449. A 450. A 451. A 452. A 453. D 454. C 455. A 456. D 457. C 458. A 459. D 460. C 461. B 462. D 463. A 464. E 465. D 466. C 467. A 468. E 469. A 470. A 471. C 472. D

473. D 474. A 475. A 476. A 477. D 478. E 479. D 480. C 481. D 482. D 483. A 484. E 485. C 486. A 487. E 488. B 489. C 490. C 491. C 492. B 493. C 494. C 495. A 496. A 497. B 498. A 499. C 500. A 501. C 502. B 503. A 504. B 505. C 506. A 507. B 508. A 509. A 510. E 511. C 512. A 513. B 514. A 515. A 516. A 517. E 518. A 519. A 520. B 521. C 522. C 523. B 524. A 525. E 526. D 527. D 528. E 529. B 530. D 531. A 532. A 533. D

534. C 535. D 536. D 537. A 538. B 539. C 540. A 541. A 542. E 543. B 544. A 545. D 546. E


1