Deck 18: Reactions at the Α Carbon of Carbonyl Compounds

Question 1

Which is the most acidic hydrogen in the compound shown?

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

Answer 1

I

Question 2

Which compound contains the most acidic hydrogens?

A)CH₃CH₂CH₃
B)CH₃CH=CH₂
C)Cyclohexane
D)(CH₃)₂C=O
E)Benzene

Answer 2

(CH₃)₂C=O

Question 3

Considering only the highlighted hydrogens,list the following compounds in order of increasing acidity:

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

Answer 3

IV,V,II,I,III

Question 4

Which is the most acidic hydrogen in the compound shown?

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

Question 5

Which is the most acidic hydrogen in the compound shown?

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

Question 6

Which of the compounds listed below is more acidic than 1-butanol?

A)Ethyl acetoacetate
B)2-Butanone
C)Ethyl pentanoate
D)All of these choices.
E)Two of these choices.

Question 7

Considering only the highlighted hydrogens,list the following compounds in order of increasing acidity:

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

Question 8

Which is the most acidic hydrogen in the compound shown?

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

Question 9

Which of the following hydrogens is the most acidic?

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

Question 10

Which of the compounds listed below is more acidic than 1-butanol?

A)Diethylmalonate
B)2-Butanone
C)Ethyl pentanoate
D)All of these choices.
E)Two of these choices.

Question 11

Which of the compounds listed below is more acidic than 2-pentanol?

A)Ethyl 3-oxopentanoate
B)2-Pentanone
C)Pentanal
D)All of these choices.
E)Two of these choices.

Question 12

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

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

Question 13

Which is the most acidic hydrogen in the compound shown?

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

Question 14

Which of the compounds listed below is more acidic than 1-butanol?

A)Ethyl 2-oxocyclohexanecarboxylate
B)2-Butanone
C)Ethyl pentanoate
D)All of these choices.
E)Two of these choices.

Question 15

Which of the compounds listed below is more acidic than 1-butanol?

A)Malonic ester
B)2-Butanone
C)Ethyl pentanoate
D)All of these choices.
E)Two of these choices.

Question 16

Which of the compounds listed below is more acidic than 2-pentanol?

A)Malonic ester
B)2-Pentanone
C)Pentanal
D)All of these choices.
E)Two of these choices.

Question 17

Which of the compounds listed below is more acidic than 2-pentanol?

A)Ethyl 2-oxocyclohexanecarboxylate
B)2-Pentanone
C)Pentanal
D)All of these choices.
E)Two of these choices.

Question 18

Which of the following compounds is the strongest acid?

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

Question 19

Which of the compounds listed below is more acidic than 2-pentanol?

A)Diethyl malonate
B)2-Pentanone
C)Pentanal
D)All of these choices.
E)Two of these choices.

Question 20

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

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

Question 21

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

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

Question 22

Which of the following represent tautomers?

A)
B)
C)
D)All of these choices.
E)None of these choices.

Question 23

Which structure represents an ester enolate?

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

Question 24

Which of the following represent keto-enol tautomers?

A)
B)
C)
D)More than one of these choices.
E)None of these choices.

Question 25

Which of the following would undergo racemization in base?

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

Question 26

Which of these halides is predicted to alkylate malonic ester (as the anion)in highest yield?

A)CH₃I
B)C₆H₅Br
C)(CH₃)₃CCH₂Cl
D)CH₃CHClCH₃
E)All of these choices should be equally effective.

Question 27

Which of these compounds would exist primarily in an enol form?

A)
B)
C)
D)
E)

Question 28

Which of these compounds would exist primarily in an enol form?

A)
B)
C)
D)
E)

Question 29

Which of the following would undergo racemization in base?

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

Question 30

Simple enols are less stable than the tautomeric keto forms because:

A)severe angle strain exists in the enol forms.
B)fewer atoms are coplanar in the keto form.
C)the enol cannot be chiral.
D)the C-C $\pi$ bond is weaker than the C-O $\pi$ bond.
E)Actually,simple enols are the more stable.

Question 31

Which of the following is a keto-enol tautomeric pair?

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

Question 32

Which of the following would not undergo racemization in base?

A)(S)-2-phenylbutanal
B)(S)-3-phenylbutanal
C)(S)-3-phenyl-2-butanone
D)(S)-3-methyl-2-phenylbutanal
E)All of these choices will undergo racemization in base.

Question 33

Which of these compounds would exist in an enol form to the greatest extent?

A)
B)
C)
D)
E)

Question 34

Which of the following is a keto-enol tautomeric pair?

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

Question 35

Which of these compounds would exist primarily in an enol form?

A)
B)
C)
D)
E)

Question 36

Which of these compounds would exist primarily in an enol form?

A)
B)
C)
D)
E)

Question 37

Which of the following would undergo epimerization in acid?

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

Question 38

Considering only the highlighted hydrogens,list the following compounds in order of increasing acidity:

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

Question 39

Which of the following would undergo epimerization in base?

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

Question 40

Which of the following is a keto-enol tautomeric pair?

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

Question 41

Which compound would be formed when 2-methylbutanal is treated with a solution of NaOD in D₂O?

A)
B)
C)
D)
E)

Question 42

What would be 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

Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of NaOD in D₂O?

A)
B)
C)
D)
E)

Question 45

Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of D⁺ in D₂O?

A)
B)
C)
D)
E)

Question 46

What would be the major product of the following reaction?

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

Question 47

What would be the major product of the following reaction?

A)
B)
C)
D)
E)

Question 48

What would be the major product of the following reaction?

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

Question 49

Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of NaOT in T₂O?

A)
B)
C)
D)
E)

Question 50

What would be the major product of the following reaction?

A)
B)
C)
D)
E)

Question 51

Which would be formed when 2-methylpropanal is dissolved in D₂O containing D⁺?

A)
B)
C)
D)
E)

Question 52

Which would be formed when 2-methylpropanal is dissolved in D₂O containing NaOD?

A)
B)
C)
D)
E)

Question 53

What would be the major product of the following reaction sequence?

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

Question 54

Which of the following would not undergo racemization in base?

A)(R)-3-methyl-4-heptanone
B)(R)-3-methyl-2-heptanone
C)(R)-4-methyl-2-heptanone
D)(R)-2,4-dimethyl-3-heptanone
E)All of these choices will undergo racemization in base.

Question 55

What would be the major product of the following reaction sequence?

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

Question 56

Which compound would be formed when 2-methylbutanal is treated with a solution of NaOT in T₂O?

A)
B)
C)
D)
E)

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 would be the major product of the following reaction sequence?

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

Question 59

Which would be formed when 2-methylpropanal is dissolved in T₂O containing NaOT?

A)
B)
C)
D)
E)None of these choices.

Question 60

Which compound would be formed when 2-methylbutanal is treated with a solution of D⁺ in D₂O?

A)
B)
C)
D)
E)

Question 61

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq.),1-bromopentane,potassium tert-butoxide,iodomethane,hot aqueous NaOH,HCl,and heat.What is the final product?

A)2-Methylheptanoic acid
B)3-Methylhexanoic acid
C)3-Methylpentanoic acid
D)2-Methylpentanoic acid
E)Ethyl 2-methylheptanoate

Question 62

What would be the major product of the following reaction sequence?

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

Question 63

What would be the major product of the following reaction sequence?

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

Question 64

What would be the major product of the following reaction?

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

Question 65

What product is finally formed when the initial compound formed from cyclohexanone and pyrrolidine is mixed with allyl chloride and that product is heated and then hydrolyzed?

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

Question 66

What would be the major product of the following reaction sequence?

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

Question 67

What would be the major product of the following reaction sequence?

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

Question 68

What would be the major product of the following reaction?

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

Question 69

What would be the major product of the following reaction sequence?

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

Question 70

What would be the major product of the following reaction sequence?

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

Question 71

What would be the major product of the following reaction?

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

Question 72

What would be the major product of the following reaction?

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

Question 73

What would be the major product of the following reaction?

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

Question 74

What would be the major product of the following reaction?

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

Question 75

What would be the major product of the following reaction?

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

Question 76

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq.),ethyl bromide,potassium tert-butoxide,isobutyl chloride,hot aqueous NaOH,HCl,and heat.What is the final product?

A)4-Ethyl-2-methylpentanoic acid
B)6-Methylheptanoic acid
C)2-Ethyl-3-methylpentanoic acid
D)2-Ethyl-4-methylpentanoic acid
E)Ethylisobutylmalonic acid

Question 77

What would be the major product of the following reaction sequence?

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

Question 78

What would be the major product of the following reaction?

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

Question 79

What would be the major product of the following reaction sequence?

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

Question 80

What would be the major product of the following reaction?

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