DiscoverFreshman Organic Chemistry 236. [gr]α-Reactivity and Condensation Reactions
36. [gr]α-Reactivity and Condensation Reactions

36. [gr]α-Reactivity and Condensation Reactions

Update: 2012-04-02
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As in many synthetic procedures, an important challenge in ketone alkylation is choosing reagents and conditions that allow control of isomerism and of single vs. multiple substitution. [gr]β-Dicarbonyl compounds allow convenient alkylation and preparation of ketones and carboxylic acids. The aldol condensation, in which an [gr]a-position adds to a carbonyl group to generate a [gr]β-hydroxy- or an [gr]α,β-unsaturated carbonyl compound, can be driven to completion by removal of water. The Robinson annulation reaction is an important example of conjugate addition to [gr]α,β-unsaturated carbonyl compounds. [gr]α-Acylation of esters as in the Claisen condensation is a key step in the biosynthesis of fatty acids. Determining the constitutional structure of sugars posed a daunting challenge to early carbohydrate chemists.

Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu

This course was recorded in Spring 2011.
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36. [gr]α-Reactivity and Condensation Reactions

36. [gr]α-Reactivity and Condensation Reactions

J. Michael McBride