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Project OCH

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4Draw the product of the following reaction.

6Draw aniline and the product of its bromination. Consider tribromination.



8Draw the structure of the Meisenheimer complex which is the intermediate of the following reaction.



10Draw the major product of the reaction proceeding upon irradiation with UV light. Consider monobromination only.

11Draw the major product of the reaction proceeding upon irradiation with UV light. Consider monobromination only.

12Draw all the products of the reaction proceeding upon irradiation with UV light. Consider monochlorination only. Do notconsider stereoisomers.


13Draw all the possible products of the reaction proceeding upon UV irradiation. Consider monochlorination only.

14Draw all the possible products of the reaction proceeding upon UV irradiation. Consider monochlorination only. Also,consider possible stereoisomers.

15Draw all the possible products of the reaction proceeding upon UV irradiation. Consider monochlorination only.


16Draw all the possible products of the reaction under UV irradiation. Consider monochlorination only.

17Draw 1-isopropyl-1-methylcyklopentane and the major product of radical bromination. Consider monobromination only.


18Draw 2,2,4-trimethylpentane and the major product of its radical bromination. Consider only monobromination.

19Draw the alkane of molecular formula C5H12 giving only one product of photochemical monochlorination.

20Draw the alkane of molecular formula C5H12 which gives three different monochlorides under the conditions ofphotochemical chlorination.


21Draw the product of the reaction of cyclohexene with N-bromosuccinimide in carbon tetrachloride.

22Draw the structure of N-bromosuccinimide, which is the agent used for radical brominations.


23Draw 1-methylnaphthalene and the major product of its reaction with N-bromosuccinimide.

24Draw the major product of the reaction of indane with two equivalents of N-bromosuccinimide.


25Draw the product of bromination of propene in chloroform.

26Draw the product of chlorination of propene under radical conditions (450 °C).

27Draw the product of the reaction of propene with hydrogen bromide.

28Draw the product of the reaction of 1-methylcyclohexene with hydrogen bromide.


29Draw the structure of the most stable radical of molecular formula C5H11.

30Draw the product of the reaction of 1-methylcyclohexene with hydrogen bromide in the presence of organic peroxides.

31Draw the product of the reaction between propene and hydrogen bromide in the presence of organic peroxides.


32Draw the product of the reaction of 1-methylcyclohexene with diluted sulfuric acid.

33Draw the product of the reaction of 1-methylcyclohexene with diborane followed by the reaction with hydrogen peroxide inthe presence of a base.


34Draw the product of the reaction of 1-methylcyclohexene with diborane in diglym (solvent).

35Draw the resonance structures of the cation in the picture. The cation is an intermediate of toluene nitration.

36Draw the product of the reaction of propene with bromine in water.


37Draw the product of the reaction. Show the configuration of the product.

38Draw the product of the reaction of 1-methylcyclohexene with bromine in water.

39Draw the product of cyclohexene hydrogenation.


40Draw the product of hydrogenation of 1,2-dimethylcyclohexene. Show the configuration of the product.

41Draw the structure of bromonium cation formed during the bromination of cyclohexene.

42Draw the product of ozonolysis of the alkene in the picture. See the scheme for the reaction conditions.


43Draw the structure of the ozonide formed by the reaction of ozone with the alkene in the picture.

44Write the structural formulae of the products of the reaction shown in the picture. Writte all the stereoisomers.

45Draw the product of the reaction of pent-1-ene with hydrogen bromide.


46Draw the product of the reaction of pent-1-ene with hydrogen bromide in the presence of organic peroxides.

47Draw the products of ozonolysis of 2,4,4-trimethylpent-2-ene.

48Draw the product of the reaction of but-1-yne with one equivalent of hydrogen chloride.


49Draw the product of the reaction of but-1-yne with two equivalents of hydrogen chloride.

50Draw the product of the addition of water to but-1-yne and the product of its subsequent rearrangement.


51Draw the product of hydrogenation of but-1-yne on a Lindlar catalyst.

52Draw the product of of hydrogenation of but-1-yne in the presence of platinum.

53Draw the product of hydrogenation of but-2-yne on the Lindlar catalyst. Consider the stereochemistry of the reaction.


54Draw the product of the reaction of but-2-yne with sodium in liquid ammonia. Consider the stereochemistry of the reaction.

55Draw the product of the reaction of but-1-yne with two equivalents of chlorine.


56Draw the product of the reaction of but-2-yne with one equivalent of chlorine. Consider the stereochemistry of the reaction.

57Write the products of ozonolysis of the alkyne shown in the picture.

58The given compounds are the products of ozonolysis of an alkyne. Draw the structure of the starting compound.


59Draw the product of the reaction of hex-1-yne with diluted sulphuric acid in the presence of a mercury(II) salt.

60Draw all the possible products of the reaction in the picture under UV irradiation. Consider monochlorination only.Consider the formation of stereoisomers.

61Draw 4-chlorobenzoic acid and the major product of its nitration.


62Draw the product(s) of toluene sulfonation. Consider monosulfonation only.

63Draw the product(s) of Friedel-Crafts acetylation of methyl phenyl ether (anisole). Consider monoacetylation only.



65Draw the product(s) of the following reaction.


66Draw furan and the product of its sulfonation. Consider monosulfonation only.

67Draw pyridine and the product of its monobromination.



69Draw the product of nitration of 4-nitrotoluene.

70Draw the structure of the most stable cyclohexadienyl carbocation which is the intermediate of the reaction shown in thepicture.


71Draw one of the mesomeric forms of cyclohexadienyl carbocation which is the intermediate of the reaction given. Considerthe formation of the major product only.

72Draw the structure of one mesomeric form of the cyclohexadienyl carbocation which is the intermediate of the reactiongiven.

73Draw the structure of one mesomeric form of the cyclohexadienyl carbocation which is the intermediate of the reactiongiven bellow.


74Draw the structure of one mesomeric form of the cyclohexadienyl carbocation which is the intermediate of the reactiongiven bellow.

75Draw the structure of the acylium ion formed from propanoyl chloride.

76Draw the three-dimensional structural formula of (R)-butan-2-ol.

77Draw the three-dimensional structural formula of (S)-but-3-en-2-ol.


78Draw a three-dimensional structural formula of the enantiomer of the compound in the picture.

79Draw three-dimensional structural formulae of the diastereomers of the compound in the picture.

80Draw a three-dimensional structural formula of the enantiomer of the compound in the picture.


81Draw three-dimensional structural formulae of the diastereomers of the compound in the picture.

82Draw a three-dimensional structural formula of the enantiomer of the compound shown.

83Draw a three-dimensional structural formula of the meso form of the compound shown.


84Draw a three-dimensional structural formula of the given compound.

85Draw a three-dimensional structural formula of the given compound.

86Draw a three-dimensional structural formula of (1R,2R)-1-bromo-2-chlorocyclopropane.


87Draw the three-dimensional structural formula of D-erythrose.

88Draw the three-dimensional structural formula of (2R,3R)-tartaric acid.

89Draw the three-dimensional structural formula of L-alanine.

90Draw the three-dimensional structural formula of (2R,3R)-2-bromo-3-chlorobutane.


91Draw the product of the reaction of 2-bromopentane with sodium iodide in acetone.

92Draw the product of the reaction of 1-iodopentane with sodium cyanide.



94Draw 1-bromo-3-chloropropane and the product of its reaction with one equivalent of sodium cyanide.



96Draw the three-dimensional structural formula of (R)-2-bromo-1-phenylbutane and the product of its reaction with sodiumiodide in acetone.

97Draw the three-dimensional structural formula of (S)-2-bromopentane and product(s) of its solvolysis in ethanol.



99Draw the intermediate of solvolysis of 1-bromo-1-methylcyclohexane in methanol.

100Draw the major product of the following reaction.

101Draw the product of the reaction of butan-1-ol with hydrogen bromide.


102Draw the product of the reaction of butan-1-ol with potassium bromide in the presence of sulfuric acid.

103Draw pentan-1-ol and the product of its reaction with hydrogen chloride.


104Draw the products of the reaction of butan-1-ol with sodium. Use the first box for the organic and the second box for theinorganic product.



106Draw 1-methylcyclohexanol and the major product of its reaction with sulfuric acid.

107Draw the products of the reaction of 1-methylcyclohexanol with sulfuric acid.

108Draw the product(s) of the following reaction.


109Draw 4-toluenesulfonyl chloride (tosychloride, TsCl) and the product of its reaction with 2-phenylethanol.

110Draw the products of the reaction of phenol with hydroxide anion.


111Draw the organic products of the reaction of methyl phenyl ether with excess hydrogen bromide.

112Draw the product of the reaction of dibutyl ether with excess hydrogen bromide.

113Draw oxirane and the product of its reaction with ammonia.


114Draw the product of the reaction of oxirane with methylmagnesium iodide followed by acidification.



116Draw 1-bromo-1-methylcyklohexane and the major product of its reaction with sodium ethoxide.

117Draw the major product of the reaction of 3-bromopentane with sodium ethoxide at elevated temperature.

118Draw the products of the reaction of 2-bromopentane with sodium ethoxide. Consider both substitution and elimination.


119Draw the major product of the following reaction.

120Draw the product of the reaction of 2,3-dibromopentane with zinc.



122Draw the product of the reaction of 1-bromopropane wih sodium tert-butoxide.

123Draw the product of the reaction of 1,2-dibromopropane with sodium amide.


124During the following reaction the initially formed carbocation undergoes a rearrangement. Draw the structures of thestarting and rearranged carbocations.

125Draw the organic product of the reaction of butylmagnesium bromide with water.


126Draw the products of the reaction of butylmagnesium bromide with but-1-yne.

127Draw the product of the reaction of butylmagnesium bromide with ethanal and subsequent acidification.


128Draw the product of the reaction of butylmagnesium bromide with acetone and subsequent acidification.


129Draw the product of the reaction of phenylmagnesium bromide with butanal and subsequent acidification.


130Draw the product of the reaction of phenylmagnesium bromide with 1-phenylpropan-2-one and subsequent acidification.


131Draw the product of the reaction of phenylmagnesium bromide with ethyl formate and subsequent acidification.

132Draw phenyllithium and the product of its reaction with deuterium oxide.


136Draw the product of the reaction of phenylmagnesium bromide with ethyl acetate and subsequent acidification.



140Draw diethyl fumarate and the product of its reaction with buta-1,3-diene. Consider stereochemistry.

141Draw the starting compounds for the preparation of the shown cyclohexene derivative by Diels-Alder reaction.


142Draw the starting compounds for the preparation of the shown cyclohexene derivative by Diels-Alder reaction.

143Draw diethyl trans-4,5-dimethylcyclohex-4-ene-1,2-dicarboxylate and suggest the starting compounds for its preparation byDiels-Alder reaction.

144Draw the resonance structure of the following carbocation.




147Draw the product of the reaction of 2,3-dimethylbuta-1,3-diene with hydrogen chloride at low temperature.


148Draw the product of the reaction of 2,3-dimethylbuta-1,3-diene with hydrogen chloride at higher temperature.

149Draw the product of the reaction of cyclopentadiene with hydrogen chloride.

150Draw the product of the reaction of butanal with sodium borohydride followed by the reaction with water.


151Draw the product of the reaction of butanal with hydrogen catalyzed by nickel.

152Draw the product of the acid-catalyzed reaction of butanal with two equivalents of methanol.

153Draw the product of the acid-catalyzed reaction of butanal with ethylene glycol.


154Draw the product of the acid-catalyzed reaction of butanal with sodium cyanide.

155Draw the product of the reaction of butanal with chromium(VI) oxide.

156Draw the product of the reaction of methyl phenyl ketone with sodium borohydride followed by the reaction with water.


157Draw the product of the reaction of methyl phenyl ketone with zinc amalgam in the presence of hydrochloric acid.

158Draw the product of the reaction of methyl phenyl ketone with sodium acetylide followed by the reaction with dilutedsulfuric acid.


159Draw the product of the reaction of methyl phenyl ketone with butylamine.

160Draw the product of the reaction of methyl phenyl ketone with aniline.

161Draw the product of the following reaction. Show the configuration of the product.


162Draw the product of the reaction of propanoic acid with lithium aluminium hydride followed by the reaction with water.

163Draw the product of the reaction of propanoic acid with ethanol catalysed by sulfuric acid.

164Draw the product of the reaction of propanoic acid with sodium hydroxide.


165Draw the product of the reaction of propanoic acid with thionyl chloride.

166Draw the product of the reaction of propanoic acid with phosphorus tribromide.

167Draw the product of the reaction of benzoic acid with sodium carbonate.


168Draw the product of the reaction of benzoic acid with diazomethane.

169Draw acetyl chloride and the products of its reaction with phenol in the presence of triethylamine.


170Draw butanoyl chloride and the products of its reaction with excess ammonia.

171Draw benzoyl chloride and the products of its reaction with excess diethylamine.


172Draw maleic anhydride and the product of its reaction with ammonia.

173Draw propanoic anhydride and the product of its reaction with water.


174Draw butanoic anhydride and the products of its reaction with ethanol catalysed by sulfuric acid.



176Draw the product of the reaction of ethyl propanoate with methylmagnesium bromide (2 equivalents) followed byacidification.

180Draw anisole and the product(s) of its monobromination.


181Fill in the mechanism of the reaction of toluene with bromine in the presence of iron(III) bromide.


182Draw 1,4-dimethylcyclohexene and the product of its reaction with diluted sulfuric acid.


187Fill in the mechanism of acid-catalyzed hydrolysis of ethyl acetate.


188Fill in the intermediates of the hemiacetal formation from benzaldehyde.


189Draw (S)-2-bromopentane and the product of its reaction with sodium iodide in acetone.


190Fill in the mechanism of the reaction of propan-1-ol with hydrogen bromide.


191Fill in the intermediates of the dehydration of 1-methylcyclohexanol.


192Fill in the mechanism of the reaction of methyl phenyl ether with hydrogen bromide.


193Draw trans-2-bromo-1-methylcyclohexane in the conformation suitable for the elimination of hydrogen bromide and theproduct of its reaction with sodium ethanolate.

194Draw the products of the reaction of butylmagnesium bromide with ethanol.


195Fill in the intermediates of the acetal formation from the benzaldehyde hemiacetal.


196Draw the product of pyridine bromination.

198Draw the product of the reaction of hexanal with chromium(VI) oxide.


200Draw aniline and the product of its tribromination.

203Draw the product of the reaction of triethylamine with hydrogen chloride.


204Draw the product of the reaction of diisopropylamine with butyllithium.

205Draw all the products of the reaction of toluene with potassium permanganate. Do not forget all the byproducts.

206Draw the product of the reaction of butanenitrile with lithium aluminium hydride.


207Draw the product of the reaction of p-tert-butylnitrobenzene with hydrogen on a platinum catalyst.

208Draw the product of the reaction of 1-bromo-2-phenylethane with sodium azide.


209Draw the product of the reaction of 3-phenylpropylazide with lithium aluminium hydride.

210Draw all the organic products of Hoffmann rearrangement of phenylacetamide.

211Draw all the products of Curtius rearrangement of benzoyl azide.


2122-Phenylethylamine can be prepared by a reduction. Suggest synthesis of this compound from an alkyliodide. The synthesishas two steps.Target molecule.

The first step is substitution of alkyliodide with sodium azide. Draw the starting compound (alkyliodide) and the product.

The azide is then reduced. Draw the structure of at least one possible reducing agent.

214Draw the product of the reaction of 2,4,6-trinitrochlorobenzene with hydroxide anion.


215From the following structures choose the ones which can undergo a substitution of chlorine atom with hydroxide anion.

216Show by means of resonance structures the stabilization of intermediate carbanion in the substitution of2-nitrochlorobenzene with hydroxide anion. The reaction proceeds by addition-elimination mechanism.

Next, draw the resonance structure which also show the stabilization of the carbanion by the nitro group.


217A mixture of two products is formed by the reaction of p-bromotoluene with sodium hydroxide. Draw the unstableintermediate and the final products.Draw the starting compound.

p-Bromotoluene reacts with a base (NaOH).

The benzyne next adds a molecule of water.


218Draw the intermediate and all products of the reaction of bromobenzene with potassium amide. The bromobenzene islabeled by a radioactive isotope 14C in position one.


219When furan is added to the mixture of bromobenzene and potassium amide, a so called intermediate trap is created tocapture the intermediate of the elimination reaction (bromobenzene with potassium amide). Explain this process bychemical equations.

220Draw the product of the bromination of propylbenzene with N-bromosuccinimide.


221Draw the products (including inorganic ones) of the reaction of pentan-2-ol with thionyl chloride.

222Draw the products (including inorganic ones) of the reaction of cyclopentanol with phosphorus tribromide.


223Describe the mechanism of radical monochlorination of toluene.Initiation.

The first propagation step.

The second propagation step.

Termination.

224From the following structures choose the ones which can undergo oxidation with an inorganic oxidation agent (KMn04,CrO3, Na2Cr2O7).


225Pyridinium chlorochromate (PCC) is a selective oxidation agent used for the oxidation of alcohols. Draw the structure ofPCC.

226Draw the product of the oxidation of but-3-en-1-ol with PCC (pyridinium chlorochromate).

227Which alcohol could you oxidize to get the product shown below?


228Which alcohol could you oxidize to get the product shown below?

229What products will you get by the oxidation of hexane-1-ol using PCC or CrO3 in an aqueous acid?The product of oxidation with PCC.

The product of oxidation with CrO3 in an aqueous acid.

230Draw the product of phenol oxidation with potassium dichromate.


231Draw the products (including inorganic ones) of the reaction of methanol with sodium.

232Draw the product of the reaction of phenylsulfonic acid with sodium hydroxide at 300 °C.


233Draw the organic products of the reactions of pentan-1-ol with the following agents.

Reaction with PBr3.

Reaction with SOCl2 (thionyl chloride).

Reaction with chromium trioxide in an aqueous sulfuric acid.

Reaction with PCC (pyridinium chlorochromate).


234Rank the following phenols according to their decreasing acidity.

The most acidic phenol.

Less acidic phenol.

The least acidic phenol.


235p-Benzoquinone is a very good dienophile in Diels-Alder reactions. What product will you get from its reaction with oneequivalent of butadiene?

What product will you get from the reaction of p-benzoquinone with two equivalents of butadiene?


236Rank the following ethers according to their increasing boiling points.

Ether with the lowest boiling point.

Higher boiling point (the second one).

Ether with the highest boiling point.


237Rank the following acids according to their increasing acidity.

The least acidic compound.

More acidic (the second) compound.

The most acidic compound.


2381-Chloroanthraquinone reacts with methoxide anion. Draw the structure of a Meisenheimer complex and the final product.

239Chlorobenzene usually does not react with nucleophiles. However, at high temperatures and high pressure phenol is formedby elimination-addition mechanism. First, draw the product of elimination and then the product of the addition of water tothe unstable intermediate.


240A mixture of three products is formed during the reaction of m-bromotoluene with NaOH. Draw the unstable intermediatesand the final products.Draw the starting compound.

m-Bromotoluene reacts with a base (NaOH).

Next, a molecule of water adds to the benzynes .


2411-chloro-4-nitrobenzene reacts with deuterated sodium hydroxide. Draw the intermediate adduct and the product.


242What products are formed by the reaction of 2,6-dideuterochlorobenzene with sodium amide in ammonia. First, draw thereactive intermediate.


243What product is formed by the reaction of 4-methyl-2-nitrochlorobenzene with potassium benzylthiolate? First, draw thestarting compound.

The starting compound reacts with the base - benzylthiolate anion.


244What product is formed by the reaction of 2,4-dinitrochlorobenzene with hydrazine in triethylene glycol? First, draw thestarting compound.

The starting compound reacts with the base - hydrazine. The molecular formula of the product is C6H6N404.


245What product is formed by the reaction of 1,3-dichlorobenzene with a mixture of nitric and sulfuric acids, and then withammonia in ethylene glycol? The molecular formula of the final product is C6H6N4O4.First, draw the starting compound.

Now the reaction with a mixture of nitric acid and sulfuric acid.

Then the reaction with excess ammonia.


246What product is formed by the reaction of 4-(trifluoromethyl)chlorobenzene with a mixture of nitric and sulfuric acid andthen with sodium methoxide in methanol? The molecular formula of the final product is C8H6F3NO3.First, draw the starting compound.

Now the reaction with a mixture of nitric acid and sulfuric acid.

Then the reaction with a base - sodium methoxide.


247What product is formed by the reaction of 4-methoxy-2-methylchlorobenzene with N-bromosuccinimide in CCl4 and thepresence of organic peroxides and then with sodium methylthiolate? The molecular formula of the final product isC9H11BrOSFirst, draw the starting compound.

Now the reaction with NBS.

Then the reaction with a base - sodium methylthiolate.


250How does p-bromobenzyl bromide react with sodium cyanide. First, draw the starting compound.

Now the reaction with cyanide anion.

251From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C:chlorobenzene and o-nitrochlorobenzene. First, draw both compounds.

Now choose the more reactive substrate.


252From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C:o-nitrochlorobenzene and m-nitrochlorobenzene. First, draw both the compounds.


253From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C:4-chloro-3-nitroacetophenone and 4-chloro-3-nitrotoluene. First, draw both the compounds.



254The preparation of the pesticide chlorobenside is composed of several steps. The first step is the reaction of4-(chloromethyl)nitrobenzene with 4-chlorothiophenolate anion.

Now the thioether reacts with iron in HCl and then with NaOH.

The amine (a derivative of aniline) reacts first with sodium nitrite in hydrochloric acid, and next with copper(I) chloride.


255Draw the three-dimensional structural formula of (2R,3R)-butane-2,3-diol.

256Draw the three-dimensional structural formula of (2R,3S)-butan-2,3-diol.

257Draw the structural formula of (Z)-3,4-dimethylhex-3-ene.

258Draw the structural formula of (E)-3,4-dichlorohex-3-ene.

259Draw the structural formula of (E)-hex-3-ene.


260Draw both possible chair conformers of trans-1,4-dimethylcyclohexane.

261Draw cis-1,3-dimethylcyclohexane and trans-1,3-dimethylcyclohexane in three-dimensional structures. Use wedged bondsto indicate the position of the methyl groups.


262Rank the following acids according to the increasing acidity.


The acid second in the order of acidity.



263All the following acetic acid derivatives react with ammonia upon formation of acetamide. Rank these derivatives accordingto the decreasing reactivity.

The most reactive derivative.

The derivative which is the second in the order of reactivity.

The least reactive derivative.


264Rank the following amines according to the increasing basicity.

The least basic amine.

The amine which is the second in the order of basicity.

The most basic amine.


265Rank the following amines according to the increasing basicity.

The least basic amine.

The amine which is the second in the order of basicity.

The most basic amine.


266Draw the product of the reaction of propylbromide with thiourea.

Next, draw the product its hydrolysis by hydroxide ions.

267Draw the products of the reaction of butanethiol with sodium hydroxide.

From the equation above choose the compound with pKa = 10.


268Draw the product of the reaction of propane-1,3-dithiol in the presence of oxygen and iron(III) chloride.

269What product is formed by the reaction of dodecylbromide with thiourea, followed by the reaction with sodium hydroxide?Draw the product.

270Draw the product for the reaction of p-nitrophenylacetonitrile with water in the presence of sulfuric acid.


271Draw the product of the reaction of pentanenitrile with water in the presence of hydroxide ions.

272In two steps draw the reaction of benzonitrile and butylmagnesium bromide in diethyl ether.


273What product is formed by the reaction of pyridine-3-carboxamide by phosphorus(V) oxide?

274Draw the structure of the most stable radical with the molecular formula C7H7.

275Draw the structure of the most stable radical derived from cyclohexene.

276Draw all the possible dichloroderivatives formed by radical chlorination of cyclopentane. Do not consider stereoisomerism.


277Draw the major product of the monosulfochlorination of propane.

278Draw the major product of the nitration of propane.


279Draw the intermediates in the synthesis of a nitrile from benzoic acid.


280What product is formed by the reaction of 1-methyl-2-cyclohexene-1-one with benzylthiol?

281Write the equation for the reaction of cyclopentanol with p-toluenesulfonyl chloride.

282Write the equation for the reaction of 3-chlorobut-1-ene with methanethiolate anion.


283Draw the products of the reaction of methyl phenyl sulfide with sodium periodate. First, draw the starting compounds.

Second, draw the products.

284Draw the products of the reaction of methyl vinyl sulfide with hydrogen peroxide in acetic acid. First, draw the startingcompounds.

Second, draw the products.


285Draw the product of the reaction of dodecyl methyl sulfide with methyl iodide.

286Write the equation for the reaction of sodium benzenethiolate with methyl iodide.

287Draw the chemical formulas of the following heterocyclic compounds. First, pyrrole.

Furane.

Thiophene.


288Draw furane and the product of its reaction with dioxane dibromide. First, draw the starting compound.

289Draw pyrrole and the product of its nitration. First, draw the starting compound.


290Draw thiophene and the product of its acylation. First, draw the starting compound.

291Draw three resonance structures which support the hypothesis of electrophilic substitution proceeding at position two of thepyrrole ring.


292Rank the following heterocycles according to the increasing basicity.

The least basic heterocycle.

The heterocycle which is the second in the order of basicity.

The most basic heterocycle.


293Draw pyridine and the product of its nitration. Consider mononitration only.

Next, draw the product.

294Draw the products (organic and inoganic) of the reaction of 4-chloropyridine with sodium ethoxide.

295Draw the products (organic and inorganic) of the reaction of 2-chloropyridine with amide anion.


296Write a simplified mechanism of the reaction of 2-chloropyridine with amide ion.

Draw the intermediate of the addition of amide ion to the aromatic ring.

297From the following two compounds choose the ones which are NOT aromatic.


298From the following two compounds choose the ones which ARE aromatic.


299Draw the products of the reactions of 4-methylpyridine with the following agents.


300Draw the products of the reactions of 1-methyl-4-nitronaphthalene with the following agents.


301Draw the products of the reaction of the following ketal with the indicated agents.


302Anisole (methyl phenyl ehter) and sodium benzoate both undergo Birch reduction by sodium in liquid ammonia. Draw theproducts of both reactions.

303Write the equation for the reaction of dimethylamine with sodium nitrite in the presence of hydrochloric acid.


304


305Draw the products of the reactions of bromine with the following substrates.

306Write the equation for the reaction of pyrrolidine with sodium nitrite in the presence of hydrochloric acid.


307Write the mechanism of the reaction of propylamine with sodium nitrite in an acidic medium.

The reaction proceeds with the transfer of a hydrogen cation.

Next, reaction with another hydrogen cation (the reaction proceeds in an acidic medium).

All the preceding products are not isolable. Now, draw the isolable (although unstable) product formed by the elimination ofwater.


308Draw the product of the reaction of 2-propylamine with sodium nitrite in the presence of hydrochloric acid.

309Draw the product of the reaction of N,N-dimethylaniline with sodium nitrite in the presence of hydrochloric acid.


310Draw the product of the reaction of N-methylaniline with sodium nitrite in the presence of hydrochloric acid.

311Draw the product of the reaction of aniline with sodium nitrite in the presence of hydrochloric acid.


312Write the products of the reactions of phenyldiazonium chloride with the following agents.


313Draw the products of the reaction of phenyldiazonium chloride with the following agents.


314Draw the products of the reaction of p-isopropylphenyldiazonium hydrogen sulfate with the following agents.


315Draw the products of the reaction of p-methylphenyldiazonium chloride with the following agents.

316Write the equation for the reaction of phenyldiazonium ion with phenol.


317Write the equation for the reaction of p-nitrophenyldiazonium ion with anisole (methyl phenyl ehter).

318Draw the product of the reaction of p-methylphenyldiazonium ion with benzene in the presence of sodium hydroxide.


319Draw the intermediates in the synthesis of 2-bromo-1-iodobenzene from benzene. If two products are formed, choose theone leading to the product.


320Draw the intermediates in the synthesis of 3-fluorophenyl ethyl ketone from benzene.


321Draw the intermediates in the synthesis of the following azo compound from naphthalene.


322Draw the product of the reaction of benzaldehyde with methylamine.

323Draw the product of the reaction of cyclohexanone with isobutylamine.


324Describe the course of the reaction of cyclopentanone with ethylamine. First, draw the intermediate adduct.

325Draw the product of the reaction of acetone with dimethylamine.


326Draw the product of the reaction of acetophenone with diethylamine. First, draw the intermediate adduct.


327Describe the course of the reaction of cyclohexanone with tetrahydropyrrole. First, draw the intermediate adduct.

328Draw the formula of methylenetriphenylphosphorane. Do not forget the charges.


329Draw the product of the reaction of cyclohexanone with methylidenetriphenylphosphorane.

330Describe the course of the reaction of phenyl methyl ketone with methylidenetriphenylphosphorane. First, draw the cyclicoxaphosphetane.


331Write the equation for the reaction of triphenylphosphine with 2-chloropropane.

332Write the equation for the reaction of triphenylphosphine with methyl bromide.


333Draw the product of the reaction of benzaldehyde with cyclopentylidenetryphenylphosphorane.

334Draw the product of the reaction of triphenylphosphine with ethyl bromide and the product of the successive reaction withbutyllithium.


335Draw the products of the reaction of methyl triphenyl phosphonium bromide with dimsyl sodium (sodium salt ofdimethylsulfoxide).

336Draw the product of the reaction of triphenylphosphine with chlorocyclopentane.


337Draw the product of the reaction of cyclohexanone with chlorine in an aqueous medium.

338Draw the product of the reaction of cyclohexanecarbaldehyde with bromine in chloroform.

339Draw the keto and enol forms of acetone.

340Draw the keto and enol forms of cyclopentanone.


341Write the products of the reaction of acetone (in its enol form) with bromine.


342Describe the mechanism of halogenation of cyclopentanone in an acidic medium.An enol form of cyclopentanone is formed in the first step. Draw the starting cyclopentanone and the structure of its enolform.

Next, write both resonance forms of the intermediate formed by the reaction of the enol with bromine.

The intermediate is deprotonated by a base.

343Draw the keto and enol forms of 2,4-pentanedione and then choose the one which is more stable.

Now draw the form which is more stable.


344Describe the mechanism of the reaction of acetone with hydroxide ion in an aqueous medium and the formation of enolate.

Next, draw the formation of the enol form.

How will the enol form react with water?


345Write the equation for the reaction of 2-methyl-1,3-cyclopentadione with hydroxide anion. First, draw the formation of acarbanion.

Now, draw all the other resonance structures of the carbanion formed in the reaction.

346Draw all the products of the reaction of acetophenone with bromine in the presence of sodium hydroxide.

347Draw all the products of the reaction of cyclopentyl methyl ketone with bromine in the presence of hydroxide ions.


348Draw the structures of intermediates and products formed in the aldolization of butanal.

349What product is formed by heating 2-ethyl-3-hydroxyhexanal?


350Draw the product which is formed when heating acetophenone (phenyl methyl ketone) in the presence of tert-butoxide ionsin xylene at 100 °C.

351Draw the product of the reaction of but-1-ene with meta-chloroperoxybenzoic acid.

352Meta-chloroperoxybenzoic acid is used for epoxidation of alkenes. Draw its chemical formula.


353Draw the product of the following reaction. Draw the correct stereochemistry.




356Draw the product of the oxidation of cyclohexanone with peroxyacetic acid.

357Draw the product of the oxidation of acetophenone with peroxyacetic acid.

358Draw all the products of the oxidation of hexane-2,3,4-triol with potasium periodate.


359Draw the product of the oxidation of cyclohexane-1,2-diol with potasium periodate.

360A radical cation is formed by the reaction of acetone with magnesium. Draw the structure of the radical anion.

Draw the product of the coupling reaction between two radical anions followed by the reaction with water.


361A radical anion is formed as an intermediate in the reaction of benzene with sodium in liquid ammonia and methanol. First,draw the structure of the radical anion.

Next, draw the structure of the final product.

362The reaction of butanal with aniline in the presence of sodium cyanoborohydride leads first to an imine, which issubsequently reduced. First, draw the structure of the imine.

Next, draw the structure of the final product obtained by the reduction of the imine with sodium cyanoborohydride.


3632-Phenylethylamine can be prepared by reduction with lithium aluminium hydride. Suggest two possible startingcompounds which do not contain an oxygen atom.

364Describe the mechanism of the nitration of chlorobenzene.


365Draw the structure of the electrophile formed in the reaction of toluene with propene in the presence of acidic catalyst.Then, draw the products of the reaction.

Draw the possible products of monosubstitution.

366Draw 1-methylnaftalene and the product of its monobromination.



368Draw the product of the sulfonation of naphtalene at 25 °C.

369Draw the product of the sulfonation of naphtalene at 160 °C.


370Draw thiophene and the product of its sulfonation.

371Draw thiophene and the product of its reaction with peroxobenzoic acid.


372Draw the intermediate and the final product of the addition of bromine to cyclohexene. Show the configuration of theproduct.


373Draw the mechanims of hydroxymercuration of cyclohexene followed by reductive work-up of the adduct.


374Draw the mechanims of hydroxymercuration of1-methylcyclohexene followed by a reductive work-up of the adduct.


375Draw butano-4-lactone and the product of its reaction with ammonia.


376Draw the product of the reaction of benzoyl chloride with sodim acetate.

377Draw the product of the reaction of butanamide with bromine in the presence of sodium hydroxide.


378Fill in the mechanism of alkaline hydrolysis of acetamide.


379Draw the mechanism of the hydrolysis of benzoylchloride.


380Fill in the mechanism of the reaction between acetanhydride and ethanol under acidic conditions.


381Fill in the mechanism of the reaction of propanoic acid with ethanol in the presence of mineral acid.


382Draw the products of the thermal cleavage of the following N-oxide.


383Draw the major product of the thermal cleavage of the following acetate.


384Describe the mechanism of the dehydration of pinacol.


385When pentanamide reacts with bromine in the presence of a hydroxide, an isocyanate is formed. The reaction proceeds withthe addition of water and decomposition of the carbamoic acid. Draw the structures of the intermediates and the finalproduct.

Structure of the isocyanate:

Structure of the carbamoic acid:

Final products, including the inorganic products:

386Draw the product of the reaction of butanal with hydroxylamine.


387Write the equation for the reaction of acetone with dimethylamine.

388Fill in the course of the reaction of cyclopentanone with hydroxylamine. First, draw the primary adduct.

389Draw the product of the reaction of cyclohexanone with hydrazine.


390Draw the product of the reaction of acetophenone with hydrazine and the product of its successive heating with potassiumhydroxide.

391Draw furan and maleic anhydride and the product of their reaction.


392Draw the structures of the intermediates and the products of the aldol reaction of propanal.

393Draw the product of the heating of acetone in the presence of barium hydroxide.


394Draw the structures of the intermediates and the products of the aldol reaction of phenylacetaldehyde.


395Draw the structures of the intermediates and the products of the aldol reaction of propanal with benzaldehyde catalyzed by abase (EtONa).


396Draw the product of heating of hexane-2,5-dione in the presence of sodium hydroxide.

397Draw the products of heating of 3-methylhexane-2,5-dione in the presence of sodium hydroxide.


398Draw the structures of the intermediates and the products of the aldol reaction of cyclopentanone.


399Suggest the starting compounds for the preparation of the following product by aldol condensation.

400Suggest the starting compounds for the preparation of the following product by aldol condensation.


401Draw the intermediates and the products of Claisen condensation of ethyl propanoate in the presence of sodium ethoxide.


402Draw the intermediates and the products of Claisen condensation of ethyl phenylacetate in the presence of sodium ethoxide.


403Draw the intermediates and the products of Claisen condensation of cyclohexanone with ethyl formate in the presence ofsodium ethoxide.


404Draw the intermediates and the products of Claisen condensation of ethyl benzoate with ethyl acetate in the presence ofsodium ethoxide.


405Draw the product of heating of ethyl acetate in the presence of sodium ethoxide, followed by acidification.

406Draw the product of heating of diethyl heptanedioate in the presence of sodium ethoxide, followed by acidification.


407From the following compounds choose the ones which will presumably give high yields in Claisen condensation.

408Draw lithium diisopropylamide.

Now, draw the product of the reaction of lithium diisopropylamide with cyclohexanone.


409Draw ethyl-acetoacetate and the product of its reaction with one equivalent of LDA.

410Draw ethyl-acetoacetate and the product of its reaction with two equivalents of LDA.


411Draw the product of the following reaction sequence.

412Draw the product of the following reaction sequence.

413Suggest the starting compounds for the preparation of the following product by Claisen condensation.


414Draw the product of the reaction of cyclopentanone with diethylamine, followed by the reaction with methyl iodide.

415Draw the structure of 2-(4-isobutylphenyl)propanoic acid.

416Draw the structure of N-(4-nitro-2-phenoxyphenyl)methanesulfonamide.


417Draw the structure of 6-dimethylamino-4,4-diphenylheptan-3-one.

418Draw the structure of 2-bromo-2-chloro-1,1,1-trifluoroethane.

419Draw the structure of 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether.

420Draw the structure of N-(aminocarbonyl)-2-bromo-3-methylbutaneamid.

421Draw the structure of N-(3-acetylphenyl)acetamide.


422Draw the structure of 1-phenylpropane-2-amine.

423Draw the structure of (1R,2S)-1-phenyl-2-(methylamino)propan-1-ol.

424Draw the structure of (1R,2R)-1-phenyl-2-(methylamino)propan-1-ol.

425Draw the structure of 4,5-bis(bromomethyl)-3-hydroxy-2-methylpyridine.

426Draw the structure of 2-(3,4-dihydroxyphenyl)ethaneamine.


427Draw the structure of N-ethyl-3-hydroxy-N,N-dimethylbenzenammonium chloride.

428Draw the structure of 2-(diethylamino)ethyl-4-aminobenzoate.

429Draw the structure of 2-methyl-2-propyl-1,3-propanediol.

430Draw the structure of {5-[(dimethylamino)methyl]furan-2-yl}methanol.

431Draw the structure of (R)-3,5-dihydroxy-3-methylpentanoic acid.


432Draw the structure of dimethyl-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate.

433Draw the structure of 1-phenylpentan-1-ol.

434Draw the structure of methyl-3-aminopyrazine-2-carboxylate.

435Draw the structure of 4-bromo-2,2-diphenylbutane nitrile.

436Draw the structure of chloroacetyl chloride.


437Draw the structure of 4-chloro-2-benzylphenol.

438Draw the structure of diethyl 2-ethoxymethylenepropanedioate.

439Draw the structure of (E)-1-bromo-6,6-dimethylhept-2-ene-4-yne.






444Draw the structural formula of (E)-2-(bromomethyl)-3-methylhept-2-enal.

445Draw the structural formula of (E)-3-tert-butylpent-3-en-1-ol.


446Draw the structural formula of (Z)-3-bromo-3-chloro-2-(trifluormethyl)prop-2-en-1-olul.

449

450Draw water molecule.

451

452

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