Question 1

Which of the following compounds can be nitrated?

$	ext{I: Benzene}$
$	ext{II: Nitrobenzene}$
$	ext{III: Toluene}$
$	ext{IV: Ethyl acetate}$

A) Compound I only
B) Compound II only
C) Compounds I and III
D) Compounds I, II, and IV

Accepted Answer

Compounds I and III

Question 2

The compound below is prepared by reductive amination. Which carbonyl compound and which amine can be used?

$	ext{Structure: cyclohexanone + benzylamine}$

A) acetophenone and benzylamine
B) cyclohexanone and benzylamine
C) 1-phenyl-2-propanone and methylamine
D) benzaldehyde and aniline

Accepted Answer

cyclohexanone and benzylamine

Question 3

Identify the product of the following reaction:

$	ext{Cyclopentanone} + 	ext{PhNHNH_2} ightarrow$

A) I
B) II
C) III
D) IV

Accepted Answer

III

Question 4

What is the most probable outcome of the following reduction?

$	ext{Cyclohexanone} \xrightarrow{1. NaBH_4 \, 2. H_2O}$

A) Cyclohexanol
B) Cyclohexene
C) Cyclohexanone
D) Cyclohexylamine

Accepted Answer

Cyclohexanol

Question 5

A common reaction (Favorskii rearrangement) converts 2-chlorocyclohexanone into salts of cyclopentanecarboxylic acids, using sodium hydroxide solution. Which is the most plausible mechanism?

A) Nucleophilic aromatic substitution
B) Ring contraction via enolate formation
C) Aldol condensation
D) Electrophilic addition

Accepted Answer

Ring contraction via enolate formation

Question 6

The aldol condensation of cyclopentanone with itself produces which of these products?

A) I
B) II
C) III
D) IV

Accepted Answer

III

Question 7

What would be the major product of the following reaction sequence? (LDA = lithium diisopropylamide)

$	ext{p-methoxyacetophenone} \xrightarrow{1. LDA \, 2. CH_3I}$

A) I
B) II
C) III
D) IV

Accepted Answer

III

Question 8

What would be the major product of the following reaction?

$	ext{Benzaldehyde} + 	ext{NaOH} ightarrow$

A) Benzyl alcohol
B) Benzoin
C) Benzoic acid
D) Benzylidene benzyl alcohol

Accepted Answer

Benzylidene benzyl alcohol

Question 9

Which product results from the conjugate addition of HCN to 2-cyclopentenone?

A) I
B) II
C) III
D) IV

Accepted Answer

III

Question 10

Cyclization reactions, such as the Dieckmann condensation, are often carried out using dilute solutions of the reagents to be cyclized. What is the most plausible reason?

A) All reactions proceed faster in high dilution
B) The intermolecular reaction is favored by high dilution
C) The intramolecular reaction is favored by high dilution
D) The intermolecular reaction is minimized at low concentration

Accepted Answer

The intramolecular reaction is favored by high dilution

Question 11

What is the most appropriate name for the following structure?

$	ext{Structure: 1,3-diphenylpropane}$

A) 1,3-diphenylpropane
B) benzylbenzene
C) 1,2-diphenylethane
D) phenylpropane

Accepted Answer

1,3-diphenylpropane

Question 12

Consider the synthesis below. What is compound Y?

$	ext{PhCOCH}_2	ext{CO}_2	ext{Et} \xrightarrow{1. NaOH/EtOH, heat \, 2. HCl, heat} ightarrow Y$

A) HOCH$_2$CO$_2$Et
B) PhCOCO$_2$OH
C) CH$_3$CH$_2$CO$_2$H
D) C$_6$H$_5$CH$_2$CO$_2$H

Accepted Answer

C$_6$H$_5$CH$_2$CO$_2$H

Question 13

The enolate of 2,4-pentanedione (triketone structure) is resonance stabilized. Which ones of the structures 1-4 are valid resonance forms of the enolate of 2,4-pentanedione?

A) 1 and 2
B) 2 and 3
C) 1, 2, and 4
D) 1, 2, 3, and 4

Accepted Answer

1, 2, and 4

Question 14

What is the likely product of an intermolecular aldol condensation of the diketone below?

$	ext{Structure: 1,3-cyclohexanedione}$

A) compound 1
B) compound 2
C) compound 3
D) compound 4

Accepted Answer

compound 3

Question 15

One way of making polymers consists of heating a strained lactone with a trace of an acidic or basic catalyst. The lactone undergoes transformation to the polymer. What is the most plausible repeat unit of the polymer?

A) I
B) II
C) III
D) IV

Accepted Answer

II

Question 16

The reaction of methylmagnesium bromide with 3-cyclohexenone results in the formation of a mixture of two products, one resulting from direct addition at the carbonyl carbon, the other from conjugate addition. Which compounds form?

A) 1 and 2
B) 2 and 3
C) 1 and 3
D) 3 and 4

Accepted Answer

1 and 2

Question 17

Three of the ketones below racemize very rapidly in acidified water while the other one remains optically pure. Which ones racemize? (Hint: they form enolates)

A) 1, 2, and 3
B) 2, 3, and 4
C) 1, 3, and 4
D) 1, 2, and 4

Accepted Answer

1, 2, and 3

Question 18

One functional group is absent. Which one?

A) ketone
B) carboxylic acid
C) ester
D) thioester

Accepted Answer

thioester

Question 19

Which aldol adduct is phenylacetaldehyde in equilibrium with?

A) 1
B) 2
C) 3
D) 4

Accepted Answer

2

Question 20

The reaction of diethyl heptanedioate with sodium ethoxide would give as the product:

A) I
B) II
C) III
D) IV

Accepted Answer

III

Organic Chemistry Problem Set: Key Concepts and Mechanisms

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