Deck 19: Enolate Anions and Enamines

Question 1

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

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

Answer 1

4

Question 2

Which of the following are intermediates in the base catalyzed aldol reaction of propanal to form 2-methyl-2-pentenal?
1)enol
2)enolate
3)tetrahedral carbonyl intermediate
4)aldol

A)only 1 and 2
B)only 1, 3 and 4
C)only 2, 3 and 4
D)1, 2, 3 and 4

Answer 2

only 2, 3 and 4

Question 3

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

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

Answer 3

1

Question 4

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

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

Question 5

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

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

Question 6

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

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

Question 7

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 8

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

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

Question 9

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

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

Question 10

How many different $\beta$ -hydroxyaldehydes and $\beta$ -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 11

How many different $\beta$ -hydroxyaldehydes and $\beta$ -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 12

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

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

Question 13

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 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

How many different $\beta$ -hydroxyaldehydes and $\beta$ -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 17

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

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

Question 18

Which of the following are intermediates in the acid catalyzed aldol reaction of propanal to form 2-methyl-2-pentenal?
1)enol
2)enolate
3)tetrahedral carbonyl intermediate
4)aldol

A)only 1 and 2
B)only 1, 3 and 4
C)only 2, 3 and 4
D)1, 2, 3 and 4

Question 19

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 20

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

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 sequence of reactions?

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

Question 24

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

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

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

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

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

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 reaction?

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 reaction?

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

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

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

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

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

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

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

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

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

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

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

Question 49

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

Question 50

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

Question 51

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

Question 52

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

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

Question 53

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 54

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

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

Question 55

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

Question 56

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

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

Question 57

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 58

Tautomerization is catalyzed by both acids and bases.

Question 59

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

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

Question 60

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

Question 61

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

Question 62

______

Question 63

______

Question 64

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 65

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

Question 66

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

Question 67

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

Question 68

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

Question 69

______

Question 70

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 71

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

Question 72

______

Question 73

Consider the following reaction. Use this reaction to answer the following questions.

-The product of this reaction is ______.

A) a $\beta$ , $\gamma$ -unsaturated aldehyde
B) an $\alpha$ , $\beta$ -unsaturated ketone
C) an $\alpha$ , $\beta$ -unsaturated aldehyde
D) an enol

Question 74

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

Question 75

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

Question 76

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

Question 77

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

Question 78

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

Question 79

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

Question 80

_______