Deck 19: Enolate Anions and Enamines

Question 1

What is the major organic product obtained from the following reaction?

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

Answer 1

1

Question 2

What is the major organic product obtained from the following reaction?

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

Answer 2

1

Question 3

What is the major organic product obtained from the following reaction?

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

Answer 3

3

Question 4

How many different β-hydroxyaldehydes and β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and benzaldehyde with base?

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

Question 5

What is the major organic product obtained from the following reaction?

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

Question 6

How many different β-hydroxyaldehydes and β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and acetophenone with base?

A) 4
B) 6
C) 9
D) 12

Question 7

What is the major organic product obtained from the following reaction?

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

Question 8

What is the major organic product obtained from the following reaction?

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

Question 9

Which of the following compounds can be prepared by an aldol condensation by treating a single carbonyl compound with base?

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

Question 10

How many β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of acetone with base?

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

Question 11

What is the major organic product obtained from the following reaction?

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

Question 12

What is the major organic product obtained from the following reaction?

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

Question 13

How many different β-hydroxyaldehydes and β-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of butanal and acetone with base?

A) 4
B) 6
C) 9
D) 12

Question 14

Which of the following compounds can be prepared by a mixed aldol condensation by treatment of a mixture of two carbonyl compounds and NaOH?

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

Question 15

What is the major organic product obtained from the following reaction?

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

Question 16

What is the major organic product obtained from the following reaction?

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

Question 17

Which of the following compounds can be prepared by an aldol condensation by treating a single carbonyl compound with base?

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

Question 18

Which of the following compounds can be prepared by a mixed aldol condensation by treatment of a mixture of two carbonyl compounds and NaOH?

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

Question 19

What is the major organic product obtained from the following reaction?

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

Question 20

How many different aldols (β-hydroxyaldehydes), including constitutional isomers and stereoisomers, are formed upon treatment of butanal with base?

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

Question 21

What is the major organic product obtained from the following reaction?

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

Question 22

What is the major organic product obtained from the following reaction?

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

Question 23

What is the major organic product obtained from the following reaction?

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

Question 24

Which of the following carboxylic acids can be made via a malonate ester synthesis?

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

Question 25

What is the major organic product obtained from the following reaction?

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

Question 26

What is the major organic product obtained from the following reaction?

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

Question 27

What is the major organic product obtained from the following reaction?

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

Question 28

What is the major organic product obtained from the following reaction?

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

Question 29

What is the major organic product obtained from the following reaction?

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

Question 30

What is the major organic product obtained from the following sequence of reactions?

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

Question 31

What is the major organic product obtained from the following reaction?

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

Question 32

Which one of the following ketones cannot be made via an acetoacetate ester synthesis?

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

Question 33

What is the major organic product obtained from the following reaction?

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

Question 34

What is the major organic product obtained from the following reaction?

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

Question 35

What is the major organic product obtained from the following reaction?

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

Question 36

What is the major organic product obtained from the following reaction?

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

Question 37

What is the major organic product obtained from the following sequence of reactions?

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

Question 38

What is the major organic product obtained from the following reaction?

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

Question 39

What is the major organic product obtained from the following sequence of reactions?

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

Question 40

What is the major organic product obtained from the following reaction?

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

Question 41

In carbonyl condensation reactions new carbon-to-carbon bonds are formed and enolate anions can act as a nucleophiles.

Question 42

What is the major organic product obtained from the following sequence of reactions?

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

Question 43

Which combination of organic bromide(s) and dicarbonyl compound can be used to prepare the following product (in a multistep synthesis)?

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

Question 44

What is the major organic product obtained from the following sequence of reactions?

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

Question 45

What is the major organic product obtained from the following sequence of reactions?

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

Question 46

Tautomerization is catalyzed by both acids and bases.

Question 47

What is the major organic product obtained from the following sequence of reactions?

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

Question 48

The following molecule will not undergo an aldol condensation with another like molecule.

Question 49

What is the major organic product obtained from the following sequence of reactions?

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

Question 50

What is the major organic product obtained from the following sequence of reactions?

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

Question 51

Which combination of organic bromide(s) and dicarbonyl compound can be used to prepare the following product (in a multistep synthesis)?

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

Question 52

The alkyl halide that should be used to produce octanoic acid via the malonic ester synthesis is 1-bromooctane.

Question 53

An aldol condensation using 3-methylbutanal could produce the following compound.

Question 54

What is the major organic product obtained from the following sequence of reactions?

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

Question 55

What is the major organic product obtained from the following sequence of reactions?

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

Question 56

Claisen and aldol condensations can result in cyclization but the Robinson annulation cannot.

Question 57

What is the major organic product obtained from the following sequence of reactions?

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

Question 58

A 1,6-diester will produce a five-membered ring via a Dieckmann cyclization.

Question 59

Using the acetoacetic ester synthesis, to produce 5-methyl-2-heptanone, the alkyl halide that should be used is 1-bromo-2-methylbutane.

Question 60

What is the major organic product obtained from the following sequence of reactions?

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

Question 61

Consider the following types of reactions:
1. aldol condensation
2. Claisen condensation
3. Robinson annulation
4. Dieckmann condensation
5. Michael reaction

Classify the following reactions by placing the appropriate number in the blank.
______

Question 62

Consider the following reaction. Use this reaction to answer the following questions.
The product of this reaction is ______.

A) a β, γ-unsaturated aldehyde
B) an α, β-unsaturated ketone
C) an α, β-unsaturated aldehyde
D) an enol

Question 63

Consider the following types of reactions:
1. aldol condensation
2. Claisen condensation
3. Robinson annulation
4. Dieckmann condensation
5. Michael reaction

Classify the following reactions by placing the appropriate number in the blank.
______

Question 64

In an aldol reaction the following substance could be produced by the reaction of benzaldehyde and _______________. Enter the name of the substance.

Question 65

What is the major organic product obtained from the following reaction?

Question 66

Consider the following types of reactions:
1. aldol condensation
2. Claisen condensation
3. Robinson annulation
4. Dieckmann condensation
5. Michael reaction

Classify the following reactions by placing the appropriate number in the blank.
______

Question 67

Consider the following types of reactions:
1. aldol condensation
2. Claisen condensation
3. Robinson annulation
4. Dieckmann condensation
5. Michael reaction

Classify the following reactions by placing the appropriate number in the blank.
______

Question 68

What is the major organic product obtained from the following reaction?

Question 69

The class of compound formed in the reaction of the following two substance is a(n)__________.

Question 70

What is the major organic product obtained from the following reaction?

Question 71

The following compound can act as a nucleophile in an aldol reaction.

Question 72

Consider the following reaction. Use this reaction to answer the following questions.
This reaction is an example of ______.

A) an intramolecular Claisen condensation
B) an intramolecular aldol condensation
C) a Robinson annulation
D) a Michael reaction

Question 73

What is the major organic product obtained from the following reaction?

Question 74

Consider the steps in the mechanism for a base catalyzed aldol condensation. The _______ step in the base catalyzed aldol condensation is addition of an enolate to a carbonyl group.

Question 75

Consider the following types of reactions:
1. aldol condensation
2. Claisen condensation
3. Robinson annulation
4. Dieckmann condensation
5. Michael reaction

Classify the following reactions by placing the appropriate number in the blank.
_______

Question 76

In an aldol reaction the following substance could be produced by the reaction of acetone (propanone) and _______________. Enter the name of the substance.

Question 77

What is the major organic product obtained from the following reaction?

Question 78

The structure of the aldol shown below can be produced by reacting _________ with NaOH. Enter the name of the compound.
​

Question 79

In a Claisen condensation the following substance could be produced by the reaction of ethylbenzoate and _______________. Enter the name of the substance.

Question 80

A Claisen condensation could be considered to the an ester analog of an aldol condensation.