Organic Chemistry 7th Edition By Bruice – Test Bank

Chapter 11 Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

1) Which of the following is the best method for preparing CH3Br?
A) CH3OH + Br-
B) CH3OH + HBr
C) CH3OH + Br2
D) CH3OH + NaBr
E) CH3OH + Br+
Answer: B
Section: 11-1

2) Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl2)?
A) (CH3)3COH
B) CH3CH2CH2CH2OH
C) CH3CHOHCH2CH3
D) (CH3)2CHCH2OH
Answer: A
Section: 11-1

3) When 1-pentanol is heated with HCl/ZnCl2, 1-chloropentane is the major organic product. This reaction proceeds through an ________ mechanism, and ________ is produced as a byproduct.
A) SN1, H2O
B) SN2, H2O
C) SN1, H2
D) SN2, H2
E) E2, H2
Answer: B
Section: 11-1

32) When (R)-2-butanol is treated with TsCl in pyridine, the product formed is ________.
A) an achiral compound
B) a mixture of diastereomers
C) a racemic mixture
D) a single enantiomer
E) none of the above
Answer: D
Section: 11-3

44) Which of the following is least likely to be found in the product mixture which results when 2,2-dimethyl-3-pentanol is heated in phosphoric acid?
A) (E)-4, 4-dimethyl-2-pentene
B) (Z)-4, 4-dimethyl-2-pentene
C) 2, 3-dimethyl-2-pentene
D) 2, 3-dimethyl-1-pentene
E) 4, 4-dimethyl-1-pentene
Answer: E
Section: 11-4