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Introduction

When you studied the reactions of carbonyl compounds in Chapters 11 and 12, you saw that their site of reactivity is the carbonyl carbon that is attacked by nucleophiles. Aldehydes, ketones, esters, and amides have a second site of reactivity: a hydrogen bonded to a carbon adjacent to the carbonyl carbon (called an alpha-carbon) is sufficiently acidic to be removed by a base. This chapter discusses the reactions that take place at this second site of reactivity. All the reactions result from removing either a proton or CO2 from the α-carbon. Reactions at the α-carbon play an important role in several biological processes such as glycolysis, fatty acid synthesis, and the process that causes meat from older animals to be tougher than meat from younger ones.




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