Page 1168 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg
P. 1168
12.22. Formulate a mechanism for the following reaction. 1153
PROBLEMS
hv
12.23. The photochemistry of 2-benzoylcyclohexanone and its 2-alkyl derivatives
diverges. The unsubstituted compound undergoes ring cleavage, whereas the
substituted compounds result in migration of the benzoyl substituent to the
4-position of the ring. Suggest mechanisms for both reactions and account
for the effect of the alkyl substituent.
O O
O O O
O O
Ph hv Ph hv R
PhCCH 2 CCH 2 CH 2 CH CH 2
R
Ph
O
