Deck 19: Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Question 1

The reaction of diethyl heptanedioate with sodium ethoxide would give as the product:

A)I
B)II
C)III
D)IV
E)V

Answer 1

III

Question 2

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Answer 2

II

Question 3

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Answer 3

III

Question 4

Cyclization reactions,such as the Dieckmann condensation,are best carried out using fairly dilute solutions of the compound to be cyclized.Why is this so?

A)It then is possible to use less base.
B)The reagents generally are expensive.
C)A smaller amount of the compound to be cyclized can be used.
D)Intermolecular condensation is minimized at low concentration.
E)The concentration factor is unimportant.

Question 5

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 6

Which of these combinations is not one which would result in the formation of essentially one Claisen condensation product when one compound is added slowly to the mixture of the other and the base employed?

A)HCO₂Et + CH₃CH₂CO₂Et
B)PhCO₂Et + CH₃CO₂Et
C)(CO₂Et)₂ + PhCH₂CO₂Et
D)(CH₃)₃CCO₂Et + CH₃CO₂Et
E)PhCH₂CO₂Et + CH₃CO₂Et

Question 7

Why is CH₃ONa not used in the Claisen condensation of ethyl acetate?

A)CH₃O^- is a weaker base than the CH₃CH₂O^- which is used.
B)CH₃O^-Na⁺ is more difficult to prepare than CH₃CH₂O^-Na⁺.
C)CH₃O^- would abstract a proton from the ethyl group of the ester.
D)Use of CH₃O^-Na⁺ would result in transesterification.
E)CH₃O^-Na⁺ can be used as well as CH₃CH₂O^-Na⁺.

Question 8

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 9

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 10

The product(s)of the reaction of 2 mol of ethyl butanoate with sodium ethoxide is(are):

A)
B)

C)

D)

E)

Question 11

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 12

The Claisen condensation produces which of these?

A)An $\alpha$ -keto ester
B)A $\beta$ -keto ester
C)A $\beta$ -hydroxy ester
D)A $\beta$ -hydroxyaldehyde
E)A $\beta$ -diketone

Question 13

What product is formed during the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 14

The reaction of diethyl hexanedioate with sodium ethoxide would give as the product:

A)I
B)II
C)III
D)IV
E)V

Question 15

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)I and II
E)I,II,and III

Question 16

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 17

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 18

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 19

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 20

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 21

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 22

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 23

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 24

What would be the major product of the following reaction?

A)CH₃CH₂CH₂OH + CH₃CH₂COO^-
B)
C)
D)
E)

Question 25

The aldol reaction of cyclohexanone produces which of these self-condensation products?

A)I
B)II
C)III
D)IV
E)V

Question 26

What product(s)is (are)likely to be obtained upon Dieckmann condensation of the following substance?

A)I and II
B)II and III
C)III and IV
D)I and III
E)II and IV

Question 27

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 28

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 29

What is the product of the reaction:

A)I
B)II
C)III
D)IV
E)V

Question 30

What is the product of the reaction:

A)I
B)II
C)III
D)IV
E)V

Question 31

The aldol reaction of cyclobutanone produces which of these self-condensation products?

A)I
B)II
C)III
D)IV
E)V

Question 32

What is the product of the Dieckmann condensation of this diester,

A)I
B)II
C)III
D)IV
E)V

Question 33

The aldol reaction of cycloheptanone produces which of these self-condensation products

A)I
B)II
C)III
D)IV
E)V

Question 34

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 35

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 36

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 37

What would be the product of the following sequence?

A)I
B)II
C)III
D)IV
E)V

Question 38

What is the product of the reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 39

What is the expected product from the following reaction sequence?

A)I
B)II
C)III
D)IV
E)V

Question 40

The aldol reaction of cyclopentanone produces which of these self-condensation products?

A)I
B)II
C)III
D)IV
E)V

Question 41

What is the product of the Dieckmann-like condensation of this ketoester,

A)I
B)II
C)III
D)IV
E)V

Question 42

What is the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 43

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 44

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 45

Predict the product of the following reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 46

What is the product of the Dieckmann-like condensation of this ketoester,

A)I
B)II
C)III
D)IV
E)V

Question 47

What product is formed during the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 48

What would be the major product of the following reaction?

A)
B)
C)
D)
E)

Question 49

The product of the following reaction is:

A)I
B)II
C)III
D)IV
E)V

Question 50

When cyclizes in basic solution,which of these compounds will be formed?

A)I
B)II
C)III
D)IV
E)V

Question 51

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 52

What is the product of the Dieckmann-like condensation of this ketoester,

A)I
B)II
C)III
D)IV
E)V

Question 53

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 54

What is the missing reagent?

A)
B)
C)
D)
E)

Question 55

Predict the product of the following reaction sequence:

A)I
B)II
C)III
D)IV
E)V

Question 56

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 57

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 58

What is the product of the Dieckmann-like condensation of this ketoester, IV V

A)I
B)II
C)III
D)IV
E)V

Question 59

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 60

The product of the following reaction is:

A)I
B)II
C)III
D)IV
E)V

Question 61

What would be the product of the following reaction?

A)C₆H₅CH=CHCH₂CN
B)
C)
D)
E)

Question 62

What would be the product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 63

What would be the product of the following reaction?

A)

B)CH₃CH $\equiv$ CHCO₂CN
C)CH₃CH=CHCN
D)
E)

Question 64

What would be the major product of the following reaction?

A)
B)
C)
D)
E)

Question 65

Predict the major product from the following reaction:

A)I
B)II
C)III
D)IV
E)V

Question 66

What would be the product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 67

In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-methylbenzaldehyde what is the relationship between the products formed?

A)enantiomers
B)conformational isomers
C)constitutional isomers
D)diastereomers
E)unrelated

Question 68

What final product is obtained when 2,8-nonanedione is treated with base,followed by reaction with lithium aluminum hydride?

A)I
B)II
C)III
D)IV
E)V

Question 69

What product results from the intramolecular aldol reaction of 2,5-hexanedione?

A)I
B)II
C)III
D)IV
E)V

Question 70

What product(s)result from the Claisen condensation carried out with an equimolar mixture of ethyl acetate and ethyl propanoate?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 71

What final product is obtained when 2,8-nonanedione is treated with base,followed by reaction with sodium borohydride?

A)I
B)II
C)III
D)IV
E)V

Question 72

What would be the product of the following reaction sequence?

A)I
B)II
C)III
D)IV
E)V

Question 73

What would be the product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 74

What is the expected product from the following reaction sequence?

A)I
B)II
C)III
D)IV
E)V

Question 75

In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-methylbenzaldehyde how many products are possible?

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

Question 76

Predict the major product of the following reaction:

A)I
B)II
C)III
D)IV e V

Question 77

Which of these is a product of the reaction of C₆H₅MgBr with

A)
B)
C)
D)
E)

Question 78

What would be the product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 79

What would be the product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 80

What would be the product of the following reaction sequence?

A)I
B)II
C)III
D)IV
E)V