Deck 18: Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Question 1

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

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

Answer 1

I

Question 2

Which is the most acidic hydrogen in the compound shown?

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

Answer 2

II

Question 3

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

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

Answer 3

II

Question 4

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 5

Which compound contains the most acidic hydrogens?

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

Question 6

Which is the most acidic hydrogen in the compound shown?

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

Question 7

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

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

Question 8

Which of the following hydrogens is the most acidic?

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

Question 9

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

A)

B)

C)

D)

E)

Question 10

Which of the following compounds is the strongest acid?

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

Question 11

Which of the following represent keto-enol tautomers?

A)

B)

C)

D) More than one of these
E) None of these

Question 12

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

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 is the most acidic hydrogen in the compound shown?

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

Question 15

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 16

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 17

Which of the following represent tautomers?

A)

B)

C)

D) All of these
E) None of these

Question 18

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 19

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 20

Which is the most acidic hydrogen in the compound shown?

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

Question 21

Explain why the following tautomer equilibrium lies far to the right.

Question 22

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 23

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 the above will undergo racemization in base.

Question 24

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

A)

B)

C)

D)

E)

Question 25

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

A)

B)

C)

D)

E)

Question 26

What would be the major product of the following reaction?

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

Question 27

Which of the following would undergo racemization in base?

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

Question 28

What synthetic strategy would accomplish the following transformation?

A) i)Br₂,H₃O⁺;ii)NaOC₂H₅,C₂H₅OH,heat
B) i)Cl₂,FeCl₃;ii)NaOC₂H₅,C₂H₅OH,heat
C) i)HCN;ii)H₃O⁺_,heat
D) i)Br₂,h $\nu$ ;ii)(CH₃)₃COK, (CH₃)₃COH,heat
E) None of the above

Question 29

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 30

What would be the major product of the following reaction?

A)

B)

C)

D)

E)

Question 31

What would be the major product of the following reaction?

A)

B)

C)

D)

E)

Question 32

What would be the major product of the following reaction?

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

Question 33

Which of the following would undergo racemization in base?

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

Question 34

What would be the major product of the following reaction?

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

Question 35

What would be the major product of the following reaction?

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

Question 36

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 the above will undergo racemization in base.

Question 37

What would be the major product of the following reaction?

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

Question 38

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

A)

B)

C)

D)

E)

Question 39

Explain why the following tautomer equilibrium lies far to the right.

Question 40

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

A)

B)

C)

D)

E)

Question 41

What would be the major product of the following reaction?

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

Question 42

The conversion of is accomplished by the use of which oxidizing agent?

A) Ag(NH₃)₂⁺
B) O₃
C) NaOCl (Cl₂ in NaOH)
D)

E) Cu⁺⁺

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 sequence?

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

Question 45

Which reagent would best serve as the basis for a simple chemical test to distinguish between CH₃CHO and CH₃COCH₃?

A) NaOI (I₂ in NaOH)
B) Br₂/CCl₄
C) C₆H₅NHNH₂
D) NaHCO₃/H₂O
E) Ag(NH₃)₂⁺

Question 46

A compound,X,C₉H₁₀O,which reacts with I₂/NaOH to give a pale yellow precipitate,gives the following ¹H NMR spectrum. Singlet,
$\delta$ 2.0
Singlet,
$\delta$ 3.0
Multiplet,
$\delta$ 7.7
Which is a possible structure for X?

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

Question 47

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-1-propanol and 2-butanol?

A) NaOI (I₂ in NaOH)
B) KMnO₄ in H₂O
C) Br₂ in CCl₄
D) Cold concd H₂SO₄
E) CrO₃ in H₂SO₄

Question 48

Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone?

A) NaOI (I₂ in NaOH)
B) Br₂/CCl₄
C) CrO₃/H₂SO₄
D) NaHCO₃/H₂O
E) Ag(NH₃)₂⁺

Question 49

What would be the major product of the following reaction?

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

Question 50

A compound,X,C₉H₁₀O,which reacts with I₂/NaOH to give a pale yellow precipitate,gives the following ¹H NMR spectrum. Singlet,
$\delta$ 2.38
Singlet,
$\delta$ 2.54
Multiplet, (centered)
$\delta$ 7.50
Which is a possible structure for X?

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

Question 51

A compound,C₅H₁₀O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these?

A)

B)

C) CH₂=CHCH₂CHOHCH₃
D)

E)

Question 52

Which reagent would best serve as the basis for a simple chemical test to distinguish between

A) NaOI (I₂ in NaOH)
B) Br₂/CCl₄
C) CrO₃/H₂SO₄
D) NaHCO₃/H₂O
E) Ag(NH₃)₂⁺

Question 53

The conversion of is accomplished by the use of which oxidizing agent?

A) Ag(NH₃)₂⁺
B) O₃
C) NaOBr (Br₂ in NaOH)
D)

E) Cu⁺⁺

Question 54

What would be the major product of the following reaction?

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

Question 55

What would be the major product of the following reaction?

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

Question 56

A negative iodoform test will be observed in the case of which of these?

A) Acetone
B) Ethanal
C) Ethanol
D) 2-Butanol
E) All of these will give a positive test.

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?

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

Question 59

The conversion of is accomplished by the use of which oxidizing agent?

A) Ag(NH₃)₂⁺
B) O₃
C) NaOI (I₂ in NaOH)
D)

E) Cu⁺⁺

Question 60

Which compound could be subjected to a haloform reaction to produce m-chlorobenzoic acid?

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

Question 61

Consider the synthesis below.What is compound Z?

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

Question 62

What is the product,W,of the following reaction sequence?

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

Question 63

Which of the following would provide the best synthesis of 3,5-dimethyl-2-hexanone?

A) Ethyl acetoacetate + NaOC₂H₅ + CH₃I;then KO-t-Bu + (CH₃)₃CCH₂Br;then NaOH;then H₃O⁺;then heat
B) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₃CBr;then KO-t-Bu + CH₃I;then NaOH;then H₃O⁺;then heat
C) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂Br;then KO-t-Bu + CH₃I;then NaOH;then H₃O⁺;then heat
D) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CHBrCH₃;then NaOH;then H₃O⁺;then heat
E) Ethyl acetoacetate + NaOC₂H₅ + CH₃I;then KO-t-Bu + (CH₃)₂CHBr;then NaOH;then H₃O⁺;then heat

Question 64

What is the product,W,of the following reaction sequence?

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

Question 65

Consider the synthesis below.What is compound Z?

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

Question 66

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Question 67

Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

A) Sodium methoxide
B) Sodium ethoxide
C) Sodium hydride
D) Potassium tert-butoxide
E) Sodium amide

Question 68

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

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

Question 69

What is the product,L,of the following reaction sequence?

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

Question 70

Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

A) Sodium methoxide
B) Sodium ethoxide
C) Sodium hydride
D) Potassium tert-butoxide
E) Lithium diisopropylamide

Question 71

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Question 72

Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?

A) Sodium methoxide
B) Sodium ethoxide
C) Sodium hydride
D) Potassium tert-butoxide
E) Lithium diisopropylamide

Question 73

What would be the product,P,of the following reaction sequence?

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

Question 74

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Question 75

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

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

Question 76

Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?

A) Sodium methoxide
B) Sodium ethoxide
C) Sodium hydride
D) Potassium tert-butoxide
E) Sodium amide

Question 77

Consider the synthesis below.What is compound Y?

A) BrCH₂CO₂Et
B) EtO-CO-CO-OEt
C) CH₃CH₂Br
D) C₆H₅CH₂Br
E) C₆H₅Br

Question 78

Predict the product of the following reaction sequence.

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

Question 79

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 should be equally effective.

Question 80

Which of the following would provide the best synthesis of 3-ethyl-6-methyl-2-heptanone?

A) Ethyl acetoacetate + NaOC₂H₅ + CH₃CH₂I;then KO-t-Bu + (CH₃)₃CCH₂CH₂Br;then NaOH;then H₃O⁺;then heat
B) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₃CCH₂Br;then KO-t-Bu + CH₃CH₂I;then NaOH;then H₃O⁺;then heat
C) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CH₂Br;then KO-t-Bu + CH₃CH₂I;then NaOH;then H₃O⁺;then heat
D) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CH₂CHBrCH₂CH₃;then NaOH;then H₃O⁺;then heat
E) Ethyl acetoacetate + NaOC₂H₅ + CH₃CH₂I;then KO-t-Bu + (CH₃)₂CHCH₂Br;then NaOH;then H₃O⁺;then heat