Organic Chemistry

Francis A. Carey
7th edition

Chapter 17

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Question 1

Arrange the compounds below in order of

increasing solubility in H2O.

A) 3 < 1 < 2
B) 2 < 3 < 1
C) 1 < 2 < 3
D) 2 < 1 < 3
Question 2

What is the name of the crown ether show at

the right?
A) 12-crown-4
B) 10-crown-5
C) 15-crown-5
D) 18-crown-6
 Question 3

Select the combination of reagents that would produce

the highest yield of ether.

A) B)

C) D)
Question 4

Which of the ethers below would produce a

mixture of bromobutane and bromoethane
when reacted with an excess of HBr?
A) (CH3CH2CH2CH2)2O
B) CH3CH2CH2OCH3 ITS D

C) BrCH2CH2CH2CH2OCH3
D) CH3CH2CH2CH2OCH3 naesa CH2
Question 5
What is the product isolated when the epoxide
at the right reacts with CH3OH and H2SO4?

A) B)

C) D)
Question 6
What is the product isolated when the epoxide
at the right reacts with HCl at 10°C?

nucleophile cl-
basic since string neuc (anion) B

A) B)

C) D)
Question 7
What is the product isolated when the epoxide
at the right reacts with NaOCH3 in CH3OH?

A) B)

C) D)
Question 8

Which combination of reagents would

accomplish the transformation shown?

A) H2O, H2SO4
B) OsO4, (CH3)3COOH, (CH3)3COH, HO-
C) NaOCH3, CH3OH
D) H2O, NaOH least susbtsituted, so basic so d
Question 9

Which combination of reagents would

accomplish the transformation shown?
acudic, h2so4

A) CH3OH, H2SO4
B) CH3I
C) NaOCH3, CH3OH
D) O3, CH3OH
Question 10

Which of the ethers below has only singlets in

its 1H-NMR spectrum?

A) B)

C) D)
Question 11

Which of the ethers below has a coupled

doublet-septet pattern in its 1H-NMR
spectrum?

A) B)

C) D)
Question 12

The most effective pair of reagents for the

preparation of tert-butyl ethyl ether is
A) potassium tert-butoxide and ethyl
bromide.
B) potassium tert-butoxide and ethanol.
C) sodium ethoxide and tert-butyl bromide.
D) tert-butyl alcohol and ethyl bromide
Question 13

Heating a particular ether with HBr yielded a

single organic product. Which of the
following conclusions can be reached?
A) The reactant was a methyl ether.
B) The reactant was a symmetric ether.
C) The reactant was a cyclic ether.
D) Both B and C may be correct.
Question 14

An acceptable IUPAC name of the compound

shown is

butyl

A) 1-Benzyl-3-methylpentyl ethyl ether.

B) Ethyl 3-methyl-1-methylphenyl-2-hexyl
ether.
C) Ethyl 4-methyl-1-phenyl-2-hexyl ether.
D) 5-Ethoxy-3-methyl-6-phenylhexane.
Question 15

Which of the following best represents the rate-

determining transition state for the reaction
shown?

A) B)

C) D)
Question 16

What is the product of the reaction shown?

A) B)

C) D)
 Question 17
What is the product of the reaction shown of the
epoxide below with KSCH3?

A) B)

C) D)
Question 18
An important property of 18-crown-6 is its
ability to
A) act as a coenzyme in biological
oxidation-reduction reactions.
B) oxidize primary alcohols to aldehydes.
C) form a stable Lewis acid-Lewis base
complex with benzene.
D) form a stable Lewis acid-Lewis base
complex with K+.
Question 19

Which reaction is the best candidate for

catalysis by 18-crown-6? (Which reaction
proceeds faster in the presence of the crown
ether than in its absence?)
A) Bromobutane + KCN (in benzene)
B) Phenol + Br2 (in water)
C) Butanol + H2CrO4 (in water)
D) CH3CH2CH2CHO + H2 (in ethanol)
 Question 20

Which compound is benzyl isobutyl ether?

A) B)

C) D)
Answer Key – Chapter 16
1. D 11. C
2. C 12. A
3. B 13. D
4. BD 14. A
5. A 15. D
6. B 16. B
7. B 17. C
8. D 18. D
9. A 19. A
10. D 20. A