Question 1

Which of the following compounds would undergo racemization in the presence of a base?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and D)
F) C) and D)

Question 2

Will acetone be completely deprotonated by potassium tert-butoxide?

Accepted Answer

A)   Yes
B)   NoC) A) and B)
D) undefined B

Question 3

The following molecule is called: -keto ester." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   a 1,3-diketopentanoate.
B)   a diethyl malonate.
C)   an ethyl acetoacetate.
D)   a -keto ester.E) All of the above
F) A) and B)

Question 4

Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA) ?

Accepted Answer

A)   Yes
B)   NoC) A) and B)
D) undefined

Question 5

Which is the kinetic enolate of 2-methylcyclohexanone?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) None of the above
F) A) and B) C

Question 6

The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation. N1 reactions. C)  Hindered alkyl halides do not undergo SN2 reactions. D)  Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   The nucleophilic enolate requires a reaction center that has a positive charge.
B)   Hindered alkyl halides do not undergo SN1 reactions.
C)   Hindered alkyl halides do not undergo SN2 reactions.
D)   Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.E) B) and C)
F) A) and B)

Question 7

What is the starting material for the following reaction?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) All of the above
F) B) and D)

Question 8

Which of the following is an enol form of the following compound?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and B)
F) A) and C)

Question 9

Which is the most acidic proton in the following compound?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) C) and D)
F) A) and C)

Question 10

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Accepted Answer

A)   An enolate
B)   An enol
C)   A tautomer
D)   An epimerE) A) and B)
F) A) and C)

Question 11

What are the three steps in the malonic ester synthesis?

Accepted Answer

A)   Deprotonation, alkylation, hydrolysis/decarboxylation
B)   Hydrogenation, alkylation, deprotonation
C)   Alkylation, hydrolysis/decarboxylation. hydrogenation
D)   Hydrolysis/decarboxylation, deprotonation, alkylationE) All of the above
F) B) and D) A

Question 12

It has been found that -dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by:

Accepted Answer

A)   The C=C of the enol is conjugated with the carbonyl group.
B)   The -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group.
C)   Both A and B above are true.
D)   None of the choices are true.E) All of the above
F) A) and B)

Question 13

Which of the following compounds is an enol of compound X drawn below?

Accepted Answer

A)   Only I
B)   Only II
C)   Only III
D)   Only I and IIE) All of the above
F) A) and D)

Question 14

Starting with cyclohexanone, how could you prepare the diketone below? -bromoketone and then react this with the enolate of cyclohexanone. D)  Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   Treat cyclohexanone with a base under thermodynamic conditions.
B)   Hydrogenate cyclohexanone with Raney nickel.
C)   Convert cyclohexanone into the -bromoketone and then react this with the enolate of cyclohexanone.
D)   Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.E) All of the above
F) A) and C)

Question 15

What is the missing reagent in the reaction below? 2/AcOH B)  I2/KOH C)  I2 D)  KOH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   Br2/AcOH
B)   I2/KOH
C)   I2
D)   KOHE) B) and D)
F) A) and D)

Question 16

Which is the most stable form of 1,3-cyclohexanedione?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) B) and C)
F) A) and B)

Question 17

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Accepted Answer

A)   Sodium hydroxide
B)   Sodium methoxide
C)   Sodium tert-butoxide
D)   Sodium hydrideE) None of the above
F) C) and D)

Question 18

If you want to form a kinetic enolate, you want to:

Accepted Answer

A)   Use a strong, non-nucleophilic base such as LDA.
B)   Use a protic solvent.
C)   Use a low temperature.
D)   Both use a strong, non-nucleophilic base such as LDA and use a low temperature.E) All of the above
F) None of the above

Question 19

Which of the following compounds is the most acidic?

Accepted Answer

A)   Ethyl acetoacetate
B)   2-Butanone
C)   1-Butanol
D)   3-PentanoneE) None of the above
F) A) and B)

Question 20

What is the starting material in the following reaction?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and B)
F) B) and D)

Exam 23: Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Which of the following compounds would undergo racemization in the presence of a base?

Correct AnswerverifiedShow Answer

Will acetone be completely deprotonated by potassium tert-butoxide?

Correct AnswerverifiedB

The following molecule is called:

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Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA) ?

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Which is the kinetic enolate of 2-methylcyclohexanone?

Correct AnswerverifiedC

The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation.

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What is the starting material for the following reaction?

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Which of the following is an enol form of the following compound?

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Which is the most acidic proton in the following compound?

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Which of the following is the intermediate for halogenation of ketones under acidic conditions?

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What are the three steps in the malonic ester synthesis?

Correct AnswerverifiedA

It has been found that -dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by:

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Which of the following compounds is an enol of compound X drawn below?

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Starting with cyclohexanone, how could you prepare the diketone below?

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What is the missing reagent in the reaction below?

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Which is the most stable form of 1,3-cyclohexanedione?

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Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

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If you want to form a kinetic enolate, you want to:

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Which of the following compounds is the most acidic?

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What is the starting material in the following reaction?

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C

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A

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