exam three practice test

7/26/2019 Exam Three Practice Test

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CH203 Fall 2014 Exam Three Practice Test11/24/14

1. Which of the following compounds is the strongest acid?

a. CH3CH2CH2COOH

b. CH3CH2CHClCOOHc. CH3CHClCH2COOHd. ClCH2CH2CH2COOH

2. Which of the following is the strongest base?

a. iodide anion, I!

b. fluoride anion, F!

c. bromide anion, Br!

d. chloride anion, Cl!

3. Which of the following compounds has the highest pKa?

a. NH3b. H2O

c. HCld. CH4

4. Which of the following compounds has the lowest pKa?

a. H2Ob. HBr

c. NH3d. CH4

5. Which of the following compounds has the lowest pKa?a. H2Ob. H2S

c. H2Sed. H2Te

6. Which of the following is present in the highest concentration upon dissolution of H2SO4in

water?a. H2SO4

b. H+c. H3O

+

d. HO!

7. Which of the following is present in the highest concentration upon dissolution of acetic acid inwater?

a. OH!b. H3O

+c. CH3COOH

d. CH3COOH+


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8. Which of the following terms describes the reactivity of boron tribromide, BBr3?

a. Brnsted-Lowry acid and Lewis acidb. Brnsted-Lowry base and Lewis base

c. Lewis acid and nota Brnsted-Lowry acid

d. Lewis base andnot

a Brnsted-Lowry base

9. Which sets of curved arrows accounts for the protonation of propene with HI?

a. 1b. 2

c. 3d. 4

10. Which species is the conjugate acid in the following acid-base reaction?

a. 1b. 2

c. 3d. 4

11. What is the value of the equilibrium constant, Keq, for the following reaction?

a. 1013

b. 10!13c. 13

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12. Which of the following is a Lewis acid but not a Brnsted-Lowry acid?a. CH3COOH


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b. AlCl3c. H2O

d. CH3OH

13. Which of the following energy diagrams represents the slowest reaction?

a. 1

b.2c. 3

d. 4

14. Which of the following is a definition of the rate-determining step of a reaction mechanism?

a. the first stepb. the last step

c. the step that crosses the highest energy barrierd. the most exothermic step

15. Which of the following is a definition of the activation energy of a reaction?

a. the difference in Gibbs free energy between the reactants and the transition stateb. the difference in Gibbs free energy between the reactants and the intermediate

c. the difference in Gibbs free energy between the reactants and the productd. the difference in Gibbs free energy between the transition state and the product

16. Which of the following energy diagrams best represents the changes in energy during addition of

HBr to an alkene?

a. 1

b. 2c. 3


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d. 4

17. Use curved arrows to show the movement of pairs of electrons in the following acid-basereaction and show the structures of the conjugate acid and conjugate base.

18. Use curved arrows to show the movement of pairs of electrons in the following reaction between

a Lewis acid and a Lewis base, and show the structure of the product.

19. What is the major organic product obtained from the following reaction?

a. 1

b. 2c. 3

d. 4


a. 1

b. 2c. 3

d. 4



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a. 1b. 2

c. 3d. 4


a. 1b. 2

c. 3d. 4

23. What is (are) the major organic product(s) obtained from the following reaction?

1. (2R,3R)-dibromobutane2. (2S,3S)-dibromobutane

3. meso-2,3-dibromobutane

a. only 1b. only 2

c. only 3

d. only 1and 2


1. (2R,3R)-dibromobutane


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2. (2S,3S)-dibromobutane3. meso-2,3-dibromobutane

a. only 1

b. only 2

c. only3d. only 1and 2


a. 1

b. 2c. 3

d. 4


a. 1

b. 2c. 3

d. 4



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1. (2R,3R)-butanediol

2. (2S,3S)-butanediol

3. meso-2,3-butanediol

a. only1b. only 2

c. only 3

d. only 1and 2


1. (2R,3R)-butanediol2. (2S,3S)-butanediol

3. meso-2,3-butanediol

a. only 1

b. only 2c. only 3

d. only 1and 2

29. What is the best choice of reagent to perform the following transformation?

a. Br2b. HBr

c. Br2, H2Od. N-bromosuccinimide

30. What type of reactive intermediate is formed in the reaction of an alkene with Br2and water to

give a bromohydrin?a. carbocation

b. carbanionc. radical

d. cyclic bromonium ion


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31. What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid togive an alcohol?

a. carbocationb. carbanion

c. radical

d. carbene

32. Which of the following reactions of alkenes takes place with anti stereospecificity?

a. bishydroxylation (treatment with OsO4followed by NaHSO3)b. hydrogenation (treatment with H2/Pt)

c. addition of HBr (treatment with HBr)d. bromohydrin formation (treatment with Br2, H2O)

33. Which of the following reactions of alkenes takes place with syn stereospecificity?

a. addition of bromine (treatment with Br2)b. hydrogenation (treatment with H2/Pt)

c. addition of HBr (treatment with HBr)d. acid-catalyzed hydration (treatment with aqueous H2SO4)

34. What is the IUPAC name of the following compound?

a. (R)-4-methyl-2-hexyneb. (S)-4-methyl-2-hexynec. (R)-3-methyl-4-hexyne

d. (S)-3-methyl-4-hexyne


a. (E) 2-butene

b. (Z) 2-butenec. 2-butyned. 1-butyne



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a. 2-methyl-3-hexene

b. 2-methyl-3-heptynec. 2-bromo-3-methylbutane

d. 2-methyl-2-butene


a. 3,4-dibromohexane

b. 3,3-dibromohexanec. (Z) 3,4-dibromohexened. 3,3,4,4-tetrabromohexane


a. 2-hexanone

b. hexanal

c. 2-hexanold. cis-2-hexene


a. 1b. 2


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c. 3d. 4


a. 1b. 2

c. 3d. 4


a. 1b. 2

c. 3d. 4

42. What is the best choice of reagent(s) to perform the following transformation?


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a. 1 mol of Br2b. 2 mol of Br2

c. 1 mol of HBrd. 2 mol of HBr

43. What is the best choice of reagent(s) to perform the following transformation?

a. H2/Ptb. H2/Lindlar catalyst

c. Na/NH3

d. BH3; followed by H2O2, NaOH

44. What is the major organic product obtained from the following series of reactions?

a. 1b. 2

c. 3d. 4

45. What is the major organic product obtained from the following series of reactions?


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a. (Z)-2-heptene

b. (E)-2-heptenec. 1-heptene

d. heptane

46. Outline how one might achieve the following transformation, showing reagents and the isolatedintermediates in the synthetic scheme.

47. Outline how one might achieve the following transformation, showing reagents and the isolated

intermediates in the synthetic scheme.

48. Predict the products:

49. Predict the products:

HCl (1.0 equiv.)

OMe

Br2

Na or Li,NH3(liquid)

Pd, H2,

H2, Lindlar Cat

Me


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50.

51. Suggest a starting material and reagent for the reaction:

52. Predict the product and draw out the full mechanism of the reaction:

53. The following reaction gives mostly one regioisomer with only a trace of the other. Draw out the

reaction mechanism and explain the formation of the product.

54. In the following reaction, only one product is recovered. Which product is it, and why?

Provide the reaction conditions to synthesize the product from starting material A. Fill the missingcompoundIand product II. Provide the reaction mechanism for step II.

H

HO

OCH3

H

ClH

O+

Product II

Product I

(diastereomer of product I)

A

Compound I

step I

step II

OCH3

O O

HH

H2O

H2SO4

O O O

+

OCH3

OCH3

CH3OH, H2SO4

exam three practice test

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