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224 Chapter 6
Copyright © 2017 Pearson Education, Inc.
59.
a.
2,2-diethyl-3-isopropyloxirane or 3,4-epoxy-4-ethyl-2-methylhexane
b.
3-ethyl-2,2-dimethyloxirane or 2,3-epoxy-2-methylpentane
60.
OH
OH
H
2
SO
4
H
2
O
1. R
2
BH/THF
2. H
2
O
2
, HO
−
,
H
2
O
forms a carbocation
intermediate, so a
carbocation
rearrrangement
will occur
−
H and
R
2
BH
is the
electrophile,
nucleophile.
is the
61.
a.
+
O
C
CH
3
CH
3
CH
2
O
C
H
CH
3
CH
2
oxidation
b.
CH
3
CHCH
2
CH
2
CH
3
CH
3
reduction
c.
H
O
O
oxidation
62.
CH
3
CHCH CH
2
CH
3
+
H Br
CH
3
C CHCH
3
CH
3
H
+
Br
−
1,2-hydride
shift
CH
3
CCH
2
CH
3
CH
3
+
CH
3
CHCHCH
3
CH
3
Br
CH
3
CCH
2
CH
3
CH
3
Br
Br
−
2-bromo-3-methylbutane
2-bromo-2-methylbutane
63.
a.
CH
3
C OCH
3
CH
3
O
−
CH
3
C CH
3
O
CH
3
O
−
+
b.
−
CH
3
C C H
CH
3
C C
−
+
NH
2
NH
3
+
c.
−
+
CH
3
CH
2
Br
CH
3
O
CH
3
CH
2
OCH
3
Br
−
+