Question 1

What is the starting material in the following reaction?

Accepted Answer

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

Question 2

Which of the following are enol forms of ethyl acetoacetate drawn below?

Accepted Answer

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

Question 3

The following molecule is called:

Accepted Answer

A)  a 1,3-diketopentanoate.
B)  a diethyl malonate.
C)  an ethyl acetoacetate.
D)  a b-keto ester.E) A) and B)
F) A) and C)

Question 4

Which of the following compounds is the most acidic?

Accepted Answer

A)  Ethyl acetoacetate
B)  2-Butanone
C)  1-Butanol
D)  3-PentanoneE) B) and D)
F) A) and B)

Question 5

Why is the enolate of acetone less basic than the allyl anion derived from propene?

Accepted Answer

A)  Because there are more atoms in acetone
B)  Because there are more resonance structures for the enolate of acetone
C)  It isn't; the allyl anion is less basic.
D)  One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen.E) A) and D)
F) A) and B)

Question 6

What is the product of the following reaction?

Accepted Answer

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

Question 7

Which of the following four compounds is the most acidic?

Accepted Answer

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

Question 8

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.  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.   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." 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 D)
F) C) and D)

Question 9

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) A) and B)
F) A) and C)

Question 10

The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.  The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.   A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 11

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

Accepted Answer

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

Question 12

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) A) and B)
F) A) and C)

Question 13

Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

Accepted Answer

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

Question 14

Select the appropriate sequence of reactions to accomplish the following synthesis. 2, CH3CO2H; [2] Li2CO3, LiBr, DMF; [3] CH3CH2CH2CH2Br B) [1] Br2, CH3CO2H; [2] Mg, Et2O; [3] CH3CH2CH2CH2Br C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  [1] Br2, CH3CO2H; [2] Li2CO3, LiBr, DMF; [3] CH3CH2CH2CH2Br
B)  [1] Br2, CH3CO2H; [2] Mg, Et2O; [3] CH3CH2CH2CH2Br
C)  [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt
D)  [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDAE) None of the above
F) A) and D)

Question 15

Which is the kinetic enolate of 2-methylcyclohexanone?

Accepted Answer

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

Question 16

Will acetone be completely deprotonated by potassium tert-butoxide?

Accepted Answer

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

Question 17

Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?

Accepted Answer

A)  The ketone undergoes a Bayer-Villigar oxidation.
B)  The ketone is reduced.
C)  The ketone undergoes an Aldol reaction.
D)  The bromine helps to stabilize the second enolate, making the product more acidic than the starting material.E) All of the above
F) A) and C)

Question 18

Which of the following ketones will give a positive iodoform test?

Accepted Answer

A)  3-Heptanone
B)  2-Pentanone
C)  3-Hexanone
D)  CyclohexanoneE) None of the above
F) A) and D)

Question 19

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

Accepted Answer

A)  Treat cyclohexanone with a base under thermodynamic conditions.
B)  Hydrogenate cyclohexanone with Raney nickel.
C)  Convert cyclohexanone into the a-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) B) and C)
F) A) and C)

Question 20

What is the major product of the following reaction?

Accepted Answer

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

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

Which is the kinetic enolate of 2-methylcyclohexanone?

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Which of the following are enol forms of ethyl acetoacetate drawn below?

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

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Why is the enolate of acetone less basic than the allyl anion derived from propene?

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What is the product of the following reaction?

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Select the appropriate sequence of reactions to accomplish the following synthesis.

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Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?

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

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The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.

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The following molecule is called:

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Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

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What is the major product of the following reaction?

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What is the starting material in the following reaction?

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Which of the following compounds is the most acidic?

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

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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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Which of the following four compounds is the most acidic?

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What are the three steps in the malonic ester synthesis?

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Which of the following ketones will give a positive iodoform test?

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Will acetone be completely deprotonated by potassium tert-butoxide?

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