ENOLATE REACTIONS OF a-HALO CARBONYL DERIVATIVES

Several reactions formally involve enolates. but the course of the reaction is altered by the presence of reactive functionality. The Darzens glycidic ester synthesis discussed in Section 9.4.B.vi is one example. 

however, is a sufficiently good lea ing group that nucleophilic attack at the carbonyl leads to cleavage of the 0=C—CBr3 bond (via 572) to produce butanoic acid and Br3C . This carbanion rapidly deprotonates butanoic acid to produce the two final products, butanoate and a haloform (bromoform, CHBr3). This 

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