Deck 18: Enols,enolates,and the Aldol Condensation: A,b-Unsaturated Aldehydes and Ketones

Question 1

Which proton in the following molecule is the most acidic?

A) 1
B) 2
C) 3
D) 4
E) 5

Answer 1

4

Question 2

What organic molecule would you expect to be present in significant amounts under the following conditions?

A)

B)

C)

D)

E)

Answer 2

Question 3

Which major product would you expect when the following diketone undergoes aldol cyclization in base,followed by acid?

A)

B)

C)

D)

E)

Answer 3

Question 4

What reactants would be used to produce cinnamaldehyde?

A)

B)

C)

D)

E)

Question 5

What product results when the following aldol product is treated with dilute acid?

A)

B)

C)

D)

E) None of these are formed.

Question 6

What product is formed in the aldol condensation of propanal?

A)

B)

C)

D)

E)

Question 7

Predict the major organic product of the following reaction sequence.

A)

B)

C)

D)

E)

Question 8

What would you expect to result from the following reaction?

A)

B)

C)

D)

E)

Question 9

Which product would you not expect in the crossed aldol reaction between acetaldehyde and propionaldehyde?

A)

B)

C)

D)

E)

Question 10

Indicate to which side,if any,the following equilibrium lies:

A) To the right
B) To the left
C) Equally to right and left
D) Cannot be predicted
E) Major product is an enol or enolate ion,respectively

Question 11

Predict the major organic product of the following reaction.

A)

B)

C)

D)

E)

Question 12

Which of the following sets of reaction conditions will result in the following transformation?

A)

B)

C)

D)

E)

Question 13

Which set of reagents would be needed for the following conversion?

A) NaOCH₂CH₃,CH₃I
B) PhCH₂MgBr,then H₃O⁺
C) CH₃MgBr,then PhCH₂Br
D) H₃O⁺,then PhCH₂Br
E) LDA,then PhCH₂Br

Question 14

The addition of either the methyl Grignard reagent or methyllithium to camphor,followed by hydrolysis,produces a tertiary alcohol known as 2-methylisoborneol,an algal metabolite which imparts a musty odor to water at very low concentrations.However,the yield of alcohol does not exceed 50%,and large amounts of camphor are recovered from the reaction even when a large excess of the Grignard or lithium reagent are used.What would be the most plausible explanation?

A) Ketones do not react with Grignard or lithium reagents.
B) The Grignard or lithium reagent had obviously degraded during storage.
C) The mechanism requires that,for each alcohol formed,one ketone molecule must remain unreacted.
D) With hindered ketones,the organometallic reagent could function as a base rather than as a nucleophile.
E) Alcohol formed early in the reaction could form an unreactive hemiacetal with remaining ketone.

Question 15

To which side,if any,would the following equilibrium lie?

A) To the left
B) To the right
C) Equally to the left and right
D) Reaction cannot occur at all
E) Equilibrium favors a different product.

Question 16

Predict the major organic product of the following reaction sequence.

A)

B)

C)

D)

E)

Question 17

To which side,if any,would the following equilibrium lie?

A) To the left
B) To the right
C) Equally to the left and right
D) Reaction cannot occur at all
E) Equilibrium favors a different product.

Question 18

What would be the expected product of the following reaction?

A)

B)

C)

D)

E)

Question 19

What major product would you expect from the following reaction?

A)

B)

C)

D)

E)

Question 20

Predict the major organic product of the following reaction.

A)

B)

C)

D)

E)

Question 21

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 22

Predict the product of the following reaction:

A)

B)

C)

D)

E) No reaction occurs.

Question 23

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 24

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 25

Given a large excess of D₂O,what product(s)would result from the following reaction at equilibrium?

A)

B)

C)

D)

E) Both B and D would be formed.

Question 26

Which statement is true of the following reactions?

A) Reactions I and II are only acid-catalyzed.
B) Reaction I is catalyzed by either acid or base,but reaction II requires acid.
C) Reactions I and II are both base-catalyzed.
D) Reaction II is catalyzed by either acid or base,but reaction I requires acid.
E) Both reactions I and II are catalyzed by either acid or base.

Question 27

Predict the product of the following reaction:

A)

B)

C)

D)

E) both B and C

Question 28

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 29

One product of the following reaction would be:

A)

B)

C)

D)

E) None of these are correct.

Question 30

The best reactants to convert cyclohexanone to 2-methylcyclohexanone cleanly would be:

A)

B)

C)

D)

E)

Question 31

What would be the major product of the following reaction?

A)

B)

C)

D)

E)