Lecture 36 - α-Reactivity and Condensation Reactions

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: Aug. 19, 2014,   recorded: June 2011,   views: 1542
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)

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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. β-Dicarbonyl compounds allow convenient alkylation and preparation of ketones and carboxylic acids. The aldol condensation, in which an α-position adds to a carbonyl group to generate a β-hydroxy- or an 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 α,β-unsaturated carbonyl compounds. 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.

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