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Chapter 18 599
Copyright © 2017 Pearson Education, Inc.
Solutions to Problems
1.
a.
CH CH
2
CH
2
CH
3
CH
3
CH
2
b.
CH
2
OH
c.
CH
3
CH
2
CHCH
2
CH
3
CH
2
d.
CH
2
Br
2.
Ferric bromide activates
Br
2
for nucleophilic attack by accepting a pair of electrons from it. Hydrated
ferric bromide cannot do this because it has already accepted a pair of electrons from water.
H O
H
Fe
Br
Br
Br
− +
3.
Solved in the text.
4.
R O
C
R
C
O
O O
AlCl
3
R
R
C
O
−
AlCl
3
C
O
R C O
acylium ion
R OAlCl
3
C
O
5.
A carbocation rearrangement occurs in
b.
and
e.
c.
CHCH
2
CH
3
CH
3
d.
CCH
3
CH
3
CH
3
a.
CH
2
CH
3
b.
CHCH
3
CH
3
e.
CCH
3
CH
3
CH
3
f.
CH
2
CH CH
2
6.
a.
CH
3
CHCH
2
CH
2
CH
3
Cl
AlCl
3
CHCH
2
CH
2
CH
3
CH
3