A reaction for converting ketones to lactones, called the Bacyer-Villiger
reaction,
O=C1CCCCC1
O=C(OO)c1cccc(Cl)c1
Ketone
3-Chloroperbenzoic acid
O=C1CCCCCO1
Lactone 3-Chlorobenzoic acid
is used in the manufacture of plastics and pharmaceuticals. 3-Chloroperbenzoic
acid is shock-sensitive, however, and prone to explode. Also, 3-chlorobenzoic
acid is a waste product. An alternative process being developed uses hydrogen
peroxide and a catalyst consisting of tin deposited within a solid support.
The catalyst is readily recovered from the reaction mixture. (a) What would
you expect to be the other product of exidation of the ketone to lactone by
hydrogen peroxide? (b) What principles of green chemistry are addressed by use
of the proposed process?