Page 973 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

a. 957
CH 3
PROBLEMS
O
H
CH 3 80°C
+ O O
H
O O
O
b.
Ph
H
H
H H CH ODPMS 110°C H
Ph H 2
CH 2
H H CH 2 ODPMS

c.
O O
SPh 105°C PhS
+ O O
CH O
OCH 3 O 3 O

d.
H H H CH OH H
H 2 < 25°C CH OH
2
H
H H
HOCH 2 H
CH 2 OH
H
e.
CH 2
CH 3
CH 2 CH 2 CH 3
f.
CO CH 3 heat
2
CO CH 3
2
10.13. The “ene” reaction is a concerted reaction in which addition of an alkene and
an electrophilic olefin occurs with transfer of a hydrogen to the electrophile and
with a double-bond shift. For example:
O
O
CH 2 CH 2 O
CH 3 + O CH 3
CH 3 CH 3 O
O

Depict the orbital array through which this reaction can occur as a concerted
process.