AK Chap 11 ed 11 - practice problem answer key chapter 11 PDF

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practice problem answer key chapter 11...

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36) What is the correct IUPAC name for the following compound? CH3

CH3 CHOHCHCHCH(CH3)2 CH3 a) 4-isopropyl-3,4-dimethyl-2-butanol b) 2,3,4-trimethyl-4-pentanol c) 1,1,2,3-tetramethyl-4-pentanol d) 3,4,5-trimethyl-2-hexanol e) 3,4,5,5-tetramethyl-2-pentanol Answer: D 40) What is a correct IUPAC name for the following compound?

HO

OH

a) 1,2-butanediol b) isopropanol c) 1-propanol d) 1,2-propanediol e) Ethylene glycol Answer: D 46) Select the structure of benzyl methyl ether. I C H3 O C H 3

II

C H3O

III

C H

3

IV

O

CH

CH

2

O

C H

C H3

V

C H

3

C H CH

2

3

O

C H

2

C H

3

79) Which compound would have the highest boiling point? a) CH3CH2CH2CH3 b) CH3CH2OCH3 c) CH3CH2CH2OH d) (CH3)2CHOH e) HOCH2CH2OH Answer: E

82) Which compound would have the lowest solubility in water? a) Diethyl ether b) Methyl propyl ether c) 1-Butanol d) 2-Butanol e) Pentane Answer: E 84) Which compound would have the lowest boiling point?

O

I

O H

O H

II

III

C H 2O H

IV

O H

V

a) I b) II c) III d) IV e) V Answer: A 108) Which alcohol would undergo acid-catalyzed dehydration most rapidly? a) 3,3-dimethyl-1-butanol b) 2,2-dimethyl-1-butanol c) 3,3-dimethyl-2-butanol d) 2-methyl-2-butanol e) All would undergo dehydration equally rapidly. Answer: D

88) Which product(s) would you expect to obtain from the following sequence of reactions? C H

3

1 . B H 3-T H F

?

2 . H 2O 2, N aO H C H C H

C H

3

H 3C

3

O

3

O H

O H

O H

+ e n a n tio m e r I

C H 2O H

II

+ e n a n tio m e r

+ e n a n tio m e r

III

IV

V

a) I b) II c) III d) IV e) V Answer: C

91) Which would be the best way to carry out the following synthesis? ? C H 3C H 2C H C H

C H 3C H 2C H 2C H 2O H

3

Br

a) (1) HA, heat; (2) H3O+, H2O, heat b) (1) (CH3)3COK / (CH3)3COH; (2) BH3:THF, then H2O2, OHc) (1) (CH3)3COK / (CH3)3COH; (2) H3O+, then H2O, heat d) (1) KOH, C2H5OH; (2) BH3:THF, then H2O2, OHe) (1) KOH, C2H5OH; (2) HA, heat; (3) H3O+, H2O, heat Answer: B 93) Which reaction can accomplish the following transformation in good yield: ?

OH

a) H+/H2O b) oxymercuration/demercuation c) hydroboration/oxidation

d) Reaction with NaOH e) None of these choices Answer: B 105) Select the structure of the major product formed from the following reaction. H3O+

?

OH

OH OH

II

III

I

OH

OH

IV

IV

a) I b) II c) III d) IV e) V Answer: C 114) The reaction between 1-pentanol and HBr to yield 1-bromopentane is probably: a) an SN1-type reaction involving the protonated alcohol as the substrate. b) an SN2-type reaction involving the protonated alcohol as the substrate. c) an E1-type reaction involving the protonated alcohol as the substrate. d) an E2-type reaction involving the protonated alcohol as the substrate. e) an epoxidation reaction. Answer: B

121) Which of the following could be used to synthesize 2-bromobutane? a) CH3CH2CHCH2 + Br2 (aq)  b) CH3CH2CCH3 + HBr  c) CH3CH2CCH + HBr  d) CH3CH2CCH + Br2  e) More than one of these choices. Answer: B 127) Which of the following could be used to synthesize 1-bromopentane? a) CH3CH2CH2CH=CH2 + b) CH3CH2CH2CH2CH2OH c) CH3CH2CH2CH2CH2OH d) CH3CH2CH2CH2CH2OH e) CH3CH2CH2CH=CH2 +

HBr  + PBr3  + NaBr  + Br2  Br2 

Answer: B

134) What would be the major product of the following reaction sequence? H O H C H

C H 3S O 2C l 3

N aI

m e s y la te

base

?

e th a n o l

H H

I I C H

H H C H

3

H O S O 2I

I C H

3

C H

3

H

H

I

H

I

II

III

IV

a) I b) II c) III d) IV e) An equimolar mixture of I and II. Answer: B

158) The product(s) of the following reaction

3

excess HBr

is/are:

heat O

O

and

OH

Br

II

I

Br Br OH

and

Br

III

a) I b) II c) III d) IV e) None of these choices. Answer: C

165) The product(s) of the following reaction

a) I

Br O

IV

b) II c) III d) IV e) None of these choices. Answer: C

174) If cis-2-butene is treated with meta-chloroperbenzoic acid what is the final product? H

H

H3C

CH3

I

H

CH3

H3C

H

II

O

O

O

O

H3C

H

H3C

H

III

H

H

H3CH2C

H

IV

a) I b) II c) III d) IV e) None of these choices. Answer: A

178) If trans-2-bromocyclohexanol is treated with sodium hydroxide what is the major product?

a) I b) II c) III d) IV e) None of these choices. Answer: C 184) What would be the major product of the following reaction sequence?

O

CH3 O-

H3O+

?

CH 3OH

OH

I

OH

OCH3 OH

OCH3 OCH 3

OCH3

II

III

OH

IV

a) I b) II c) III d) IV e) Equal amounts of II and IV Answer: A 188) What would be the final product? O C H

3

R C O O H H 3C C

CH

2

a) (CH3)2CHCH2OCH3 ( C H 3) 2 C C H

3

b)

O CH 3 ( C H 3) 2 C C H 2 O H

c)

O C H 3 ( C H 3) 2 C C H 2 O C H 3

d)

O H ( C H 3) 2 C C H 2 O C H 3

e)

O C H3

Answer: C

p ro d u ct

C H 3O H , H A

fin a l p ro d u c t...