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230 Chapter 6
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b.
the first step (See the answer to Problem 10.)
c.
H
+
e.
the
sec-
butyl cation
d.
1-butene
f.
methanol
77.
a.
CH
2
CH
3
Br
CH
2
CH
3
HBr
b.
CH
2
CH
3
H
2
Pd/C
CH
2
CH
3
c.
CH
2
CH
3
1. R
2
BH/THF
2. HO
−
, H
2 2
O , H
2
O
CH
2
CH
3
OH
CH
2
CH
3
OH
+
(The H and OH are added to the same side.)
d.
CH
2
CH
3
Br
2
CH
2
Cl
2
Br
CH
2
CH
3
Br
Br
CH
2
CH
3
Br
(The two bromines are added to opposite sides
of the cyclohexane ring.)
78.
trans
-3-hexene
a meso compound
CH
3
CH
2
C C
CH
2
CH
3
H
H
CH
2
CH
3
Br
Br
H
H
CH
2
CH
3
Br
2
79.
cis
-3-hexene
(3
S
,4
S
)-4-bromo-3-hexanol
CH
3
CH
2
C C
H
CH
2
CH
3
H
CH
2
CH
3
OH
H
Br
H
CH
2
CH
3
(3
R
,4
R
)-4-bromo-3-hexanol
CH
2
CH
3
H
Br
H
HO
CH
2
CH
3
Br
2
+
80.
a.
OH
OH
OH
H
H
H
+
H
2
O
H
2
O
H
3
O
+
+
+
b.
H Cl
+
+
Cl
−
..
..
.. ..
Cl