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Download Essential Organic Chemistry 2nd Edition Bruice Test Bank all chapters
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Essential Organic Chemistry, 2e (Bruice)
Chapter 10 Reactions of Alcohols, Amines, Ethers, and Epoxides
1) What is the functional group in an alcohol?
A) carbon-carbon double bond
B) NH2
C) OH
D) halogen
E) COOH
Answer: C
Section: 10.1
2) Which of the following compounds does not have the molecular formula C6H14O?
A) 1-hexanol
B) 2-hexanol
C) 3-methyl-2-pentanol
D) 3-methyl-3-pentanol
E) cyclohexanol
Answer: E
Section: 10.1
A) 4-sec-hexyl-5-methyl-3-hexanol
B) 3-hydroxy-4-isobutyl-5-ethyloctane
C) 5-ethyl-4-isopropyl-3-octanol
D) 3-hydorxy-4-isobutyl-5-propylheptane
E) 3-propyl-4-isopropyl-5-heptanol
Answer: C
Section: 10.1
Answer: cis-3-sec-butylcyclopentanol
Section: 10.1
A) 5-chloro-5-ethyl-3-hexanol
B) 2-chloro-2-ethyl-4-hydroxyhexane
C) 5-chloro-5-ethyl-3-hydroxyhexane
D) 5-chloro-5-methyl-3-heptanol
E) 3-chloro-3-methyl-5-heptanol
Answer: D
Section: 10.1
A) 3-chloro-2-methylcyclohexanol
B) 2-methyl-5-chlorocyclhexanol
C) 1-chloro-4-methylcyclohexanol
D) 5-chloro-2-methylcyclohexanol
E) 2-methyl-3-chlorocyclohexanol
Answer: D
Section: 10.1
CH3CH(CH3)CH2CH(OH)CH3
A) 4-methyl-2-pentanol
B) 2-methyl-2-hexanol
C) 2-methyl-4-pentanol
D) 2-methyl-3-pentanol
Answer: A
Section: 10.1
11) Predict the major product of the reaction below and provide a stepwise mechanism which
accounts for its formation.
CH3(CH2)6CH2OH + HBr →
Answer:
Section: 10.2
12) Provide the structure of the major organic product in the reaction below.
Answer:
Section: 10.2
14) Which of the following alcohols dehydrates with the fastest rate?
A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 10.3
A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 10.3
16) Which of the following alcohols, when heated with H2SO4, will undergo dehydration more
rapidly? Explain.
Answer: b) will undergo dehydration more rapidly because it produces a secondary benzylic
carbocation, which is more stable than secondary carbocation.
Section: 10.3
Answer:
Section: 10.3
18) Rank the following alcohols in decreasing order of relative ease of dehydration:
19) Draw all likely products of the following reaction, and circle the product you expect to
predominate.
2-pentanol
Answer:
Section: 10.3
Answer:
Section: 10.3
21) Provide the structure of the major organic product of the following reaction.
Answer:
Section: 10.3
A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 10.4
25) Describe the difference between oxidation of a primary alcohol using PCC in CH 2Cl2 versus
oxidation of the same primary alcohol using Na2Cr2O7 in H2SO4.
Answer: A primary alcohol in the presence of PCC and CH2Cl2 will result in an aldehyde
product whereas the same primary alcohol in the presence of Na 2Cr2O7 and H2SO4
will result in a carboxylic acid after further oxidation.
Section: 10.4
26) Provide the structure of the major organic product in the reaction below.
Answer:
Section: 10.4
27) Provide the structure of the major organic product in the reaction below.
Answer:
Section: 10.4
29) Provide the structure of the major organic product in the reaction below.
Na 2Cr2O7
(CH3)3CCH2CH2OH ⎯⎯⎯⎯⎯⎯ →
H 2SO4
Answer: (CH3)3CCH2CO2H
Section: 10.4
30) Provide the structure of the major organic product in the reaction below.
Answer:
Section: 10.4
Answer:
Section: 10.4
33) What series of synthetic steps could be used to prepare 3-hexanol from 1-propanol?
Answer: 1) PCC
2) CH3CH2CH2MgBr
3) H3O+
or
1) HBr or PBr3
2) Mg, Et2O
3) CH3CH2CHO
Section: 10.4
35) What series of synthetic steps could be used to carry out the transformation shown below?
Answer: 1) BH3
2) H2O2, -OH
3) PCC
Section: 10.4
36) When the optically active alcohol below is oxidized by H2CrO4, the major product is
__________.
Answer:
Section: 10.4
B)
C)
D)
E)
Answer: E
Section: 10.5
A) CH3CH2CH2-O-CH2CH2CH3
B)
C)
D)
A)
B)
C)
D)
E)
Answer: D
Section: 10.6
Section: 10.6
45) What are the major products from the following reaction?
A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 10.7
46) When dipentyl ether is treated with excess HI, through what type of mechanism(s) does the
major product result?
A) SN2
B) SN1
C) both SN1 and SN2
D) E1
E) E2
Answer: A
Section: 10.7
Answer:
Section: 10.7
Answer:
Section: 10.8
49) Provide the structure of the major organic product of the following reaction.
Answer:
Section: 10.8
A) I
B) II
C) III
D) IV
E) V
Answer: A
Section: 10.8
A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 10.8
A) I
B) II
C) III
D) IV
E) V
Answer: D
Section: 10.8
A) I
B) II
C) III
D) IV
E) V
Answer: E
Section: 10.8
Answer:
Section: 10.8
Answer:
Section: 10.8
56) Provide the structure of the major organic product of the following reaction.
Answer:
Section: 10.8