651 / 912
Chapter 18 643
Copyright © 2017 Pearson Education, Inc.
96.
Br
CuLi
CH
2
CH
2
OH
CH
2
CH
2
Br
CH
2
CH
2
MgBr
H CH
3
CH
3
CHCH
2
CH
3
OH
CH
2
CH
3
CH
3
Br
2
FeBr
3
1. Li
2. CuI
1.
2. HCl
O
2
PBr
3
/pyridine
Mg Et
2
O
2. HCl
1. CH
3
CH
2
MgBr
0 ºC
NaOCl
CH
3
COOH
CH
3
CCH
2
CH
3
+
CH
2
CH
2
CCH
2
CH
3
O
−
CH
3
CH
2
CH
2
CCH
2
CH
3
CH
3
OH
HCl
C
O
C
O
O
97.
The unsplit signal at 7.1 ppm suggests that all the benzene ring hydrogens in the product are chemically
equivalent. The triplet at 1.2 ppm and quartet at 2.6 ppm indicate an ethyl group.
CH
3
CH
2
CH
3
CH
2
Cl
AlCl
3
CH
3
CH
2
CH
2
CH
3