Question 1

Which is the most acidic proton in the following compound?

Accepted Answer

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

Question 2

Which of the following is a possible enol form of 2-butanone?

Accepted Answer

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

Question 3

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

Accepted Answer

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

Question 4

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) B) and D)
F) A) and B) D

Question 5

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) B) and D)
F) All of the above

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

Question 7

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 D)
F) A) and C)

Question 8

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) A) and C)
F) None of the above

Question 9

If you want to form a thermodynamic enolate,you want to

Accepted Answer

A)  keep the reaction as cold as possible.
B)  use an aprotic solvent such as THF.
C)  use a protic solvent such as ethanol.
D)  use a carboxylic acid.E) A) and B)
F) B) and C)

Question 10

It has been found that b-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 and above are true.
D)  None of the choices are true.E) A) and B)
F) B) and D) C

Question 11

For most compounds with a single keto group in the molecule,equilibrium favors the keto form over the enol form of the compound.This is due largely to what?

Accepted Answer

A)  The C=O bond is much stronger than the C=C bond.
B)  The C=C bond is much stronger than the C=O bond.
C)  The keto form can undergo intramolecular hydrogen bonding.
D)  The enol form can undergo intramolecular hydrogen bonding.E) B) and C)
F) All of the above

Question 12

What is the starting material required to accomplish the following transformation?

Accepted Answer

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

Question 13

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) A) and B)
F) All of the above

Question 14

Which of the following four compounds is the most acidic?

Accepted Answer

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

Question 15

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

Accepted Answer

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

Question 16

What is the starting material for the following reaction?

Accepted Answer

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

Question 17

Which is the kinetic enolate of 2-methylcyclohexanone?

Accepted Answer

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

Question 18

What is the structure of X,product of the following reaction?

Accepted Answer

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

Question 19

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) All of the above B

Question 20

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Accepted Answer

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

Exam 21: Substitution Reactions of Carbonyl Compounds at the a Carbon

Which is the most acidic proton in the following compound?

Correct AnswerverifiedShow Answer

Which of the following is a possible enol form of 2-butanone?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedD

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

Correct AnswerverifiedShow Answer

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.

Correct AnswerverifiedShow Answer

What are the three steps in the malonic ester synthesis?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

If you want to form a thermodynamic enolate,you want to

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedC

For most compounds with a single keto group in the molecule,equilibrium favors the keto form over the enol form of the compound.This is due largely to what?

Correct AnswerverifiedShow Answer

What is the starting material required to accomplish the following transformation?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following four compounds is the most acidic?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the starting material for the following reaction?

Correct AnswerverifiedShow Answer

Which is the kinetic enolate of 2-methylcyclohexanone?

Correct AnswerverifiedShow Answer

What is the structure of X,product of the following reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedB

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Correct AnswerverifiedShow Answer

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D

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C

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B

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