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394 Chapter 10
Copyright © 2017 Pearson Education, Inc.
5.
Draw the major elimination product that is obtained when each of the following alcohols is heated in the
presence of
H
2
SO
4
:
a.
CH
3
CH
2
C CHCH
3
CH
3
OH CH
3
b.
CH
3
CCH
3
CH
3
CH
3
CH
2
CH
2
CH
OH
c.
CH
3
CH
2
CH
2
CH
2
CH
2
OH
d.
OH
6.
Indicate whether each of the following statements is true or false:
a.
Tertiary alcohols are easier to dehydrate than secondary alcohols.
T F
b.
Alcohols are more acidic than thiols.
T F
c.
Alcohols have higher boiling points than thiols.
T F
d.
The acid-catalyzed dehydration of a primary alcohol is an
S
N
1
reaction.
T F
e.
The Hofmann elimination reaction is an E2 reaction.
T F
7.
What products are obtained when the following ethers are heated with one equivalent of HI?
a.
CH
3
CH
2
COCH
3
CH
3
CH
3
b.
O CH
2
8.
Draw the major product of each of the following reactions:
a.
CH
3
CH
2
CH
2
NH
2
+ CH
3
CH
2
SCH
2
CH
3
CH
2
CH
3
+
CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
OH
CH
3
CH
2
CH
2
OH +
pyridine
SOCl
2
H
2
SO
4
CH
3
CH
2
CH
2
CH
2
OH
NaOCl
CH
3
COOH
0
°
C
CH
3
CH
2
CH
2
CH
2
OH
H
2
CrO
4
b.
CH
3
CH
2
CH
2
NH
2
+ CH
3
CH
2
SCH
2
CH
3
CH
2
CH
3
+
CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
OH
CH
3
CH
2
CH
2
OH +
pyridine
SOCl
2
H
2
SO
4
CH
3
CH
2
CH
2
CH
2
OH
NaOCl
CH
3
COOH
0
°
C
CH
3
CH
2
CH
2
CH
2
OH
H
2
CrO
4
c.
CH
3
CH
2
CH
2
NH
2
+ CH
3
CH
2
SCH
2
CH
3
CH
2
CH
3
+
CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
OH
CH
3
CH
2
CH
2
OH +
pyridine
SOCl
2
H
2
SO
4
CH
3
CH
2
CH
2
CH
2
OH
NaOCl
CH
3
COOH
0
°
C
CH
3
CH
2
CH
2
CH
2
OH
H
2
CrO
4
d.
2
2
3
C
2 3
+
3
2
2
3 2 2
p i e
2
4
3 2 2
NaOCl
°
3 2 2
C
2
r
4
e.
3
2 +
2 2
2
ri n
2
S
CH CH C
CH CO
0 C
2