Deck 19: Acid Derivatives

Question 1

What is the name of the following compound?

A) 2-chlorohexyl ethanoate
B) 1-chlorohexyl ethanoate
C) ethyl 2-chlorohexanoate
D) ethyl 1-chlorohexanoate

Answer 1

ethyl 2-chlorohexanoate

Question 2

Rank the following in order of decreasing rate of hydrolysis.
I. acetyl chloride
II. acetic anhydride
III. ethyl acetate
IV. acetamide

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

Answer 2

I $>$ II $>$ III $>$ IV

Question 3

What is the product of the following reactions?

A)

B)

C)

D)

Answer 3

Question 4

Saponification and neutralization of ${ }^{18} \mathrm{O}$ labeled ethyl acetate, as shown below, yields which of the following isotopically labeled products?

A)

B)

C)

D) approximately equal amounts of A and B.

Question 5

Which one of the following does not react with benzoyl chloride, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl}$ ?

A) $\mathrm{NH}_{3}$
B) $\mathrm{CH}_{3} \mathrm{NH}_{2}$
C) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}$
D) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}$

Question 6

The following tetrahedral intermediate breaks down to

A) propanoyl chloride and $\mathrm{CH}_{3} \mathrm{OH}$ .
B) propanal and $\mathrm{HCl}$ .
C) propanoic acid and $\mathrm{CH}_{3} \mathrm{Cl}$ .
D) methyl propanoate and $\mathrm{HCl}$ .

Question 7

What is the product of the following reaction sequence?

A) 2-methyl-1-pentanol
B) 2-methylpentanoic acid
C) 2-bromo-3-methylpentanoic acid
D) 4-hydroxyhexanoic acid

Question 8

Identify the monomer(s) used to make the following polymer.

A)

B)

C)

D)

Question 9

Which of the following is the tetrahedral intermediate formed in the reaction of a thioester with ammonia?

A) A
B) B
C) C
D) D

Question 10

Which of the following best represents a mechanistic step in the acid-catalyzed hydrolysis of acetonitrile?

A) A
B) B
C) C
D) D

Question 11

Which of the following is the product of the reaction shown below?

A) A
B) B
C) C
D) D

Question 12

With the stereochemistry of the starting material shown, identify the stereochemistry of 2-butanol in the following reaction sequence.

(S enantiomer)

A) (S)-2-butanol
B) (R)-2-butanol
C) racemic 2-butanol
D) meso-2-butanol

Question 13

Identify the product obtained in the hydrolysis of the following cyclic acid anhydride.

A) $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
B) $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$
C) $\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$
D) $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{O}$

Question 14

What are the hydrolysis products of the following reaction?

A) ortho-chloroaniline and $\mathrm{CH}_{3} \mathrm{CH}-\mathrm{O}$
B) chlorobenzene and
C) ortho-chloroaniline and $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{Na}$
D) chlorobenzene and $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{Na}$

Question 15

The major product from this reaction would be

A) an acid chloride
B) an anhydride
C) an amide
D) an ester

Question 16

Treatment of cocaine with hot aqueous $\mathrm{NaOH}$ would yield

A) A
B) B
C) C
D) D

Question 17

Which one of the following reacts with aqueous $\mathrm{HCl}$ to give phenol?

A) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CN}$
B) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{C}_{6} \mathrm{H}_{5}$
C) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{O}$
D) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}$