Question 1

Which is the unsaturated carbonyl compound formed by the dehydration of the following b-hydroxy carbonyl compound?

Accepted Answer

A)  I
B)  II
C)  I and II
D)  None of the choicesE) A) and B)
F) A) and C)

Question 2

What is the Aldol addition product formed from the reaction of (CH3) 2CHCH2CHO with itself? 3) 2CHCH2CHO with itself?   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) A) and B)
F) C) and D)

Question 3

What product (including stereochemistry) is formed in the following intermolecular reaction?

Accepted Answer

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

Question 4

What is the name given to an Aldol reaction between two different carbonyl compounds?

Accepted Answer

A)  Multiple Aldol reaction
B)  Crossed Aldol reaction
C)  Differential Aldol reaction
D)  Versatile Aldol reactionE) B) and D)
F) A) and C)

Question 5

What is the Aldol addition product formed from reaction of the following compound with itself?

Accepted Answer

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

Question 6

Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that

Accepted Answer

A)  the Aldol reaction involves substitution while the Claisen reaction involves addition.
B)  the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed.
C)  the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base.
D)  the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed.E) A) and B)
F) C) and D)

Question 7

What reaction type is an Aldol reaction?

Accepted Answer

A)  Nucleophilic substitution
B)  Electrophilic substitution
C)  Electrophilic addition
D)  Nucleophilic additionE) C) and D)
F) None of the above

Question 8

Which of the following compounds cannot serve as a Michael acceptor?

Accepted Answer

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

Question 9

In what situation can the yield of a single crossed Aldol product be increased?

Accepted Answer

A)  The electrophilic carbonyl component is relatively unhindered and is used in excess.
B)  The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount.
C)  The nucleophilic carbonyl component is relatively unhindered and is used in excess.
D)  The nucleophilic carbonyl component is relatively hindered and is used in limited amount.E) None of the above
F) A) and C)

Question 10

What type of esters can undergo Claisen reactions?

Accepted Answer

A)  All esters can undergo Claisen reactions.
B)  Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions.
C)  Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions.
D)  Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions.E) A) and C)
F) A) and B)

Question 11

What are the two starting materials for a Robinson annulation?

Accepted Answer

A)  an a,b-Unsaturated carbonyl compound and an enolate
B)  a b-Ketoester and an enolate
C)  a 1,5-Dicarbonyl compound and an enolate
D)  a 1,3-Dicarbonyl compound and an enolateE) A) and B)
F) A) and C)

Question 12

When is a crossed Aldol reaction said to be synthetically useful?

Accepted Answer

A)  When both carbonyl compounds have a hydrogens
B)  When both carbonyl compounds have no a hydrogens
C)  When one carbonyl compound has no a hydrogens
D)  When one carbonyl compound has no b hydrogensE) All of the above
F) A) and D)

Question 13

What is the product of the following Claisen reaction?

Accepted Answer

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

Question 14

In a Michael reaction,where does the nucleophile attack the a,b-unsaturated carbonyl component?

Accepted Answer

A)  a-Carbon
B)  b-Carbon
C)  Carbonyl carbon
D)  Carbonyl carbon and b-carbonE) B) and C)
F) None of the above

Question 15

In the correct order,what are the three steps in the mechanism of an Aldol reaction?

Accepted Answer

A)  Protonation,enolate formation,nucleophilic addition
B)  Enolate formation,protonation,nucleophilic addition
C)  Enolate formation,nucleophilic addition,protonation
D)  Nucleophilic addition,enolate formation,protonationE) B) and D)
F) None of the above

Question 16

Under basic conditions,the Aldol reaction is reversible,but dehydration is not.What is the reason for this difference in reactivity?

Accepted Answer

A)  The initial Aldol product is an alkoxide,so the reaction is not energetically downhill in either direction.
B)  The initial Aldol product is an alkoxide,so the reaction is energetically downhill going toward the product.
C)  The initial Aldol product is an alkoxide,so the reaction is energetically downhill going toward the starting materials.
D)  Water is a stable molecule.E) A) and B)
F) B) and D)

Question 17

The following reaction is an example of what type of reaction?

Accepted Answer

A)  Michael reaction
B)  Aldol self-condensation
C)  Dieckmann condensation
D)  Robinson annulationE) None of the above
F) A) and C)

Question 18

What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

Accepted Answer

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

Question 19

The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result?

Accepted Answer

A)  It undergoes elimination,since water is a good leaving group.
B)  The hydroxy group is oxidized to a carbonyl.
C)  The hydroxy group reacts with the carbonyl to form a ketal.
D)  Hydroxide is eliminated via an enolate intermediate.E) A) and B)
F) A) and C) D

Question 20

The following reaction is an example of what type of reaction?

Accepted Answer

A)  Claisen condensation
B)  Mixed Aldol reaction
C)  Robinson annulation
D)  Dieckmann condensationE) B) and C)
F) A) and B)

Exam 22: Carbonyl Condensation Reactions

Which is the unsaturated carbonyl compound formed by the dehydration of the following b-hydroxy carbonyl compound?

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What is the Aldol addition product formed from the reaction of (CH3) 2CHCH2CHO with itself?

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What product (including stereochemistry) is formed in the following intermolecular reaction?

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What is the name given to an Aldol reaction between two different carbonyl compounds?

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What is the Aldol addition product formed from reaction of the following compound with itself?

Correct AnswerverifiedB

Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that

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What reaction type is an Aldol reaction?

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Which of the following compounds cannot serve as a Michael acceptor?

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In what situation can the yield of a single crossed Aldol product be increased?

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What type of esters can undergo Claisen reactions?

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What are the two starting materials for a Robinson annulation?

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When is a crossed Aldol reaction said to be synthetically useful?

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What is the product of the following Claisen reaction?

Correct AnswerverifiedB

In a Michael reaction,where does the nucleophile attack the a,b-unsaturated carbonyl component?

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In the correct order,what are the three steps in the mechanism of an Aldol reaction?

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Under basic conditions,the Aldol reaction is reversible,but dehydration is not.What is the reason for this difference in reactivity?

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The following reaction is an example of what type of reaction?

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What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

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The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result?

Correct AnswerverifiedD

The following reaction is an example of what type of reaction?

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What is the Aldol addition product formed from the reaction of (CH₃) ₂CHCH₂CHO with itself?

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B

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B

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D

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