Deck 15: Enolate Anions

Question 1

How many possible aldol products can be formed when acetone and ethanal are mixed in the presence of base?(Hint: Assume that no more than two molecules react with each other at a time.)

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

Answer 1

4

Question 2

Which ester is likely to undergo a Claisen condensation to give this product?

A) ethyl 2-methylpropanoate
B) ethyl butanoate
C) butyl ethanoate
D) 2-methylpropyl ethanoate

Answer 2

ethyl butanoate

Question 3

How many possible Claisen condensation products are formed when ethyl propanoate and ethyl methanoate are mixed with sodium ethoxide?

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

Answer 3

2

Question 4

Which of the following compounds can be used in an aldol self reaction to make a product with 5 or more carbon atoms?
I. ethanal
II. propanone (acetone)
III. benzaldehyde
IV. acetophenone

A) I, II
B) III, IV
C) I, III
D) II, IV

Question 5

Which pair of esters is most likely to provide a useful Claisen synthesis?

A) ethyl propanoate and ethyl ethanoate
B) ethyl benzoate and ethyl methanoate
C) ethyl ethanoate and ethyl oxalate
D) ethyl nicotinate and diethyl phthalate

Question 6

Which is the product of the series of reactions?

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

Question 7

Which compound undergoes the fastest exchange of hydrogen for deuterium when treated with D₂O and a trace of OD^-?

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

Question 8

Which is the major product from the reaction of 1,6-cyclodecanedione with hot aqueous NaOH?

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

Question 9

Which is the major product of the following reaction?

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

Question 10

Which are the most important contributing structures for the enolate formed by the treatment of 2,4-pentanedione with base?

A) I, II
B) II, III
C) III, IV
D) I, IV

Question 11

Which compounds will undergo decarboxylation upon heating?

A) I, II
B) II, III
C) III, IV
D) II, IV

Question 12

What is the major product of the following reaction?

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

Question 13

Order the molecules according to decreasing acidity.

A) II, III, IV, I
B) I, II, III, IV
C) III, IV, I, II
D) IV, II, III, I

Question 14

Which are the reactants for the aldol product shown?

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

Question 15

Which are contributing structures of the enolates formed by the treatment of butanone with base?

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

Question 16

What is the main product of the following reaction sequence?

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

Question 17

What is the order of decreasing acidity for the indicated protons (most acidic first)?

A) I, II, III, IV
B) III, IV, II, I
C) II, I, III, IV
D) IV, III, II, I

Question 18

What is the major product of the following reaction?

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

Question 19

What is the order of increasing acidity for these compounds (least acidic first)?

A) IV, III, II, I
B) IV, II, III, I
C) II, III, I, IV
D) III, II, I, IV

Question 20

Which is the major product formed in the following reaction?

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

Question 21

The following synthesis will proceed by which reaction?

A) Claisen condensation
B) Dieckmann condensation
C) Aldol addition
D) Aldol condensation reaction

Question 22

The major product of the following reaction is,

Question 23

Which is the product of the reaction of ethyl 3-phenylpropanoate with 1) sodium ethoxide, 2) aqueous
Sodium hydroxide, 3) aqueous hydrochloric acid, and 4) heat?

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

Question 24

What is the main product of the following reaction sequence?

Question 25

Which is the major product of the following series of reactions?

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

Question 26

Acetone reacts with 2 equivalents of molecular bromine (Br₂) in aqueous solution in the presence of sodium carbonate. What is the major product of this reaction sequence?

Question 27

What is the major product of the following reaction?

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

Question 28

The starting material that completes the following reaction is,

Question 29

Which is the product of the following series of reactions?

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

Question 30

What is the main product of the following reaction sequence?

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

Question 31

What is the main product of the following reaction sequence?

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

Question 32

What is the starting material of this reaction?

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

Question 33

Acetone reacts with 2 equivalents of molecular bromine (Br₂) in aqueous solution in the presence of sulfuric acid. What is the major product of this reaction sequence?

Question 34

The starting material that completes the following reaction is,

Question 35

Which is the major product of the following series of reactions?

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

Question 36

What is the main product of the following reaction sequence?

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

Question 37

The major product of the following reaction is

Question 38

What is the starting material of this reaction?

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

Question 39

How would you characterize this reaction forming fructose 1,6-bisphosphate?

A) aldol reaction
B) aldol condensation
C) Claisen condensation
D) Dieckmann Condensation

Question 40

Which is the major product of the following series of reactions?

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

Question 41

The starting material that completes the following reaction is

Question 42

The position of the most acidic hydrogen of the following compound is indicated by the arrow.

Question 43

The starting material that completes the following reaction is,

Question 44

What is the main product of the following reaction sequence?

Question 45

The major product of the following reaction is,

Question 46

The Michael addition of dimethylamine and 3-buten-2-one produces the following product

Question 47

The major product of the following sequence of reactions is

Question 48

The major product of the following reaction between acetone and ethyl benzoate (1:1 ratio) is?

Question 49

The major product of the following reaction is

Question 50

The position of the most acidic hydrogen of the following compound is indicated by the arrow.

Question 51

The major product of the reaction of two moles of ethyl benzoate with sodium ethoxide is

Question 52

The major enol form of ethyl 3-oxobutanoate is

Question 53

The condensation of acetoacetyl-CoA with acetyl-CoA is an Aldol reaction.

Question 54

The most stable enol form of 2-pentanone is

Question 55

The major product of the reaction of 2,4-pentanedione and 3-buten-2-one with ethoxide followed by hydroxide, acid, and heat sequentially, is

Question 56

The major product of the following reaction is,

Question 57

1-Cyclohexenecarbaldehyde can be produced from the following starting material and base.

Question 58

The self condensation of Acetyl-CoA to Acetoacetyl-CoA is a Claisen reaction.

Question 59

The major product of the following reaction is?

Question 60

The major product of the following reaction is,