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570 Chapter 17
Copyright © 2017 Pearson Education, Inc.
OH
NaOCl
O
CH
2
CH
3
c.
H HO
+
_
C
O
d.
1. CH
3
O
−
2. Br(CH
2
)
4
Br
CH
3
O
−
C
C
O
O
HCl
H
2
O
C
O
+
CO
2
+
H
2
O
+
CH
3
COOH
0 ºC
CH CH
CH CH OH
CH
3
O
OCH
3
CH
2
CH
3
O
OCH
3
CH
CH
2
(CH
2
)
3
Br
2 CH
3
OH
+
CO
2
OCH
3
OCH
3
OH
CHCH
2
H
H
C
O
C
O
C
O
C C
O O
C
O
C
O
1.
CH
3
H
C
O
add slowly
2. HCl
44.
Because the catalyst is a hydroxide ion rather than an enzyme, four stereoisomers will be formed since two
asymmetric centers are created in the product.
H OH
CH
2
OPO
3
C O
C O
C O
CHOH
CHO
−
CH
2
OPO
3
2
_
2
_
CH
2
OPO
3
C O
CHOH *
*CHOH
CH
2
OPO
3
2
_
2
_
OH
H
H OH
CH
CH
2
OPO
3
2
_
O
H C OH
CH
2
OPO
3
2
_
H C OH
H
CH
2
OPO
3
2
_
_
_
HO
H OH
45.
Seven
moles. The first two carbons in the fatty acid come from acetyl CoA.
Each subsequent two-carbon piece comes from malonyl CoA.
Because this amounts to 14 carbons for the synthesis of the 16-carbon fatty acid, seven moles of malonyl
CoA are required.