Bruice - Chimica Organica

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Chapter 16 539
Copyright © 2017 Pearson Education, Inc.
65. CH3 CH3 CH3
Br2
hv +
CH3
Br
CH 3
Br
Br Br
Br Br2
CH3
OCH2CH3
OCH2CH3
NCH2CH3
O
+
CH3
CH3
CH3
CH3
OH
CH 3
Br
HBr
1. R2BH/THF
2. H 2O2 , HO – , H2O
1. O3, –78 °C
2. (CH 3) 2S
H 2SO4
H2O
H2CrO4
SOCl2
CH3OH
CH3
CH2CH2OH
O
1. Li
2. CuI
3.
4. HCl
HOCl
CH3 CH2NH2
CH3CH2 OH
excess
HCl
L
K
J
I
H
G
F
E
D B C A
O
N
trace acid
tert-BuO−
CH 2CH2 CH 2 CH 2 H CH3
C
O
C
CH 2CH2 CH2 CH 2 OH CH 3
C
O
C
O
CH 2CH 2CH2CH 2 Cl CH3
C
O
C
O
CH 2CH 2CH2CH2 OCH 3 CH3
C
O
C
O
M
O
OH
CH3
OH
66. a. C O
CH2CH3
+ CH3 CH2NH3
+
b. CH3CH2CCH 3
OH
CH2CH 3
HO OCH3
e.
f.
N
H
i.
j. N
O
CH3O
CH3
OCH CH3NH
O
C O
C
+ CH CH 3
+
b
H
N
i.
. N
O
C O
H
3
O
a. C O
CH2CH3
+ CH3 CH2NH3
+
b. CH3CH2CCH 3
OH
CH2CH 3
HO OCH3
e.
f.
N
H
i.
j. N
O
CH3O
CH3
OCH CH3NH
O
CH 3
+ H2NH3
3 2 3
N
. CH O
H3
O
g.
NCH2CH3
h.
N
CH3CH 2 CH2CH 3
c.
CHCH3
d. CH3CH2CCH2CH3
OH
CH2 CH3
.
2 3
.
3 2 2 3
.
3
. 3 2 2 3
2 3
3
g.
NCH2CH3
h.
N
CH3 CH2 CH 2CH3
c.
CHCH3
d. CH3 CH2CCH2 CH3
OH
CH 2CH 3