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- dicarbonyls are the oldest of the specific enolate equivalents, and before the development of the use of lithium enolates, silyl enol ethers and enamines

-dicarbonyls are the oldest of the specific enolate equivalents, and before the
development of the use of lithium enolates, silyl enol ethers and enamines (around the
1950s-60s) they were one of the few reliable ways to alkylate a carbonyl. The scheme below
shows part of a synthesis of an isomer of menthone carried out in 1906.
A
(a) Draw a mechanism for the conversion of A to B.
(b) Draw a mechanism for the conversion of C to D.
(c) Suggest reagents and a mechanism for the conversion of D to E.
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