Deck 15: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Question 1

What is the name of the compound shown here?

A) N-methyl-N-methylpropanamide
B) N,N-dimethylaminoacrylate
C) N,N-dimethylpropanamine
D) N,N-dimethylpropanamide
E) N,N-dimethylpropenamide

Answer 1

N,N-dimethylpropenamide

Question 2

What is the name of the compound shown here?

A) acetyl benzene
B) benzene acetic ester
C) benzyl acetate
D) methyl benzoate
E) phenyl acetate

Answer 2

benzyl acetate

Question 3

Which of the following statements is not true about the reactions of carboxylic acid derivatives?

A) Carboxylic acid derivatives form a tetrahedral intermediate.
B) The weaker base will be the leaving group.
C) Less reactive derivatives can be converted directly into more reactive derivatives.
D) For a reaction to occur, the added group must be a stronger base than the group attached to the acyl group.
E) The weakest bond in the reaction is the pi bond, so it breaks first.

Answer 3

Less reactive derivatives can be converted directly into more reactive derivatives.

Question 4

Which carboxylic acid derivative is most readily hydrolyzed by aqueous base?

A)
B)
C)
D)
E) Carboxylic acid derivatives hydrolyze by the same mechanism and at the same approximate rate

Question 5

In nucleophilic acyl substitution reactions under basic conditions,____________.

A) protonation of the carbonyl group is followed by nucleophilic attack
B) loss of the leaving group is followed by formation of an acylium ion
C) an SN2 reaction occurs
D) the nucleophile must be a weaker base than the leaving group
E) nucleophilic addition to the carbonyl is followed by loss of a leaving group

Question 6

Which of the following reactions will proceed to the right?

A) excess H₂O, HCl, heat
B) phenol, HCl
C) CH₃NH₂, heat
D) NaNH₂
E) all except B

Question 7

Which of the following carboxylic acid derivatives could be used in this reaction?
For X =

A) ?Br
B) ?Cl
C) ?SCH₃
D) ?OCH₃
E) all of the above

Question 8

What are the expected products of the following reaction?

A) a, b
B) a, d
C) c, b
D) c, d
E) a, e

Question 9

Upon aqueous hydrolysis of ¹⁸O-labeled ethyl acetate, which oxygen(s) will be labeled in the final reaction mixture after mild acidification?

A)
B)
C)
D)
E)

Question 10

Which compound is the product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 11

Which set of reagents will produce the indicated product?

A) 1. H₂CrO₄ 2. SOCl₂/pyridine 3. H₂O
B) 1. TsCl/pyridine 2. NaCN 3. H₃O⁺/? 4. SOCl₂/pyridine
C) 1. Acetic anhydride 2. SOCl₂/pyridine
D) 1. Acetic acid/H₃O⁺ 2. PCl₃/pyridine
E) 1. Ethyl acetate/H₃O⁺ 2. NaCl

Question 12

Which of the following dicarboxylic acids has the most similar pK_a1 and pK_a2 values?

A)
B)
C)
D)
E)