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Chapter 17 567
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34.
No, because an intramolecular reaction would lead to a strained four-membered ring. Therefore, an
intermolecular reaction is preferred; the reaction invloves removal of a proton from the more acidic
central carbon.
HO
O
_
CH
2
CH
2
CH
3
C
O
C
CH
3
O
intramolecular product
_
CH
3
C
O
CH
3
C
O
CH
2
CH
3
C
O
O O
CH
3
CH C
OH
C
CH
3
CH
C
CH
3
intermolecular product
CH
3
CH
2
C
O
CH
3
C
O
35.
OH
O
a.
HO
O
b.
CH
OH
O
c.
OH CCH
3
O
d.
36.
a.
O
HO
−
O
O
O
O
b.
O
HO
−
O
O
O
O