L_9_09 - 318N Krische, Lecture 9: Tu - 02/17/09, Acyl...

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318N – Krische, Lecture 9: Tu - 02/17/09, Acyl Derivatives Last lecture we considered the structure of acyl derivatives: acid chlorides, esters and amides. We saw that resonance effects through π -bonds will decrease the electrophilicity of the carbonyl carbon because π -donation helps satisfy the carbonyls demand for electron density. Conversely, inductive effects through σ -bonds increase the electrophilicity of the carbonyl carbon. We conclude that acid chlorides are more electrophilic than esters, and esters are more electrophilic than amides. Acid chlorides may be prepared from carboxylic acids using SOCl 2 . Exposure of acid chlorides to alcohols results in the formation of esters. Acid chlorides will react spontaneously with alcohols to give esters via an addition-elimination mechanism (see on-line handout). We can change the nucleophilic partner in this reaction, e.g. instead of using an alcohol, we can use an amine. Through the same addition-elimination mechanism, acid chlorides will react spontaneously with amines to give amides. Again, we can change the nucleophilic partner in this reaction. The reaction of acid chlorides with carboxylic acids gives carboxylic acid anhydrides
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This note was uploaded on 03/31/2009 for the course CH 318M taught by Professor Bocknack during the Spring '08 term at University of Texas at Austin.

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L_9_09 - 318N Krische, Lecture 9: Tu - 02/17/09, Acyl...

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