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378 Chapter 10
Copyright © 2017 Pearson Education, Inc.
59.
2,3-Dimethyl-2-butanol dehydrates faster because it forms a tertiary carbocation, whereas 3,3-dimethyl-
2-butanol initially forms a secondary carbocation.
CH
3
CH CCH
3
CH
3
OH CH
3
2,3-dimethyl-2-butanol
a tertiary alcohol
CH
3
CH CCH
3
CH
3
CH
3
OH
3,3-dimethyl-2-butanol
a secondary alcohol
60.
O
2-ethyloxirane
CH
2
CH
3
a.
CH
3
CH
2
CHCH
2
OH
OH
0.1 M HCl is a dilute solution
of HCl in water.
b.
CH
3
CH
2
CHCH
2
OH
OCH
3
c.
CH
3
CH
2
CHCH
2
OH
OH
d.
CH
3
CH
2
CHCH
2
OCH
3
OH
61.
H
2
SO
4
/
or
1. HBr/
2.
tert
-BuO
−
MCPBA
or
1. Cl
2
/H
2
O
2. NaH
NaOCl
CH
3
COOH
0 ˚C
1. OsO
4
2. H
2
O
2
, H
2
O
CH
3
O
−
CH
3
O
−
HO
−
OTs
OCH
3
Br
O
TsCl
pyridine
O
OH
OH
OH
OH
OH
OH
OH
HBr/
tert
-BuO
−
+
62.
2-hexene and 3-hexene
3 2 2 2 2 2
CH CH CH CH CH CH OH
H
2
SO
4
3 2 2 2
2
CH CH CH CH CH CH
2
H O
H
+
+
3 2 2
3
CH CH CH CH CHCH
3 2 2 2
3
+
CH CH CH CH CHCH
2-hexene
+
H
+
+
3 2 2
2 3
CH CH CH CHCH CH
H
2
SO
4
+
+
3 2
2 3
3 2 2
3
+
CH CH CH CHCH CH CH CH CH CH CHCH
3-hexene
(cis and trans)
2-hexene
(cis and trans)
H