Ch_322b_18.09

Ch_322b_18.09 - Chapter 18.9 lecture note

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Nucleophilic Substitution at Acyl Carbon Aldehydes and ketones undergo nucleophilic additions to the carbonyl group: C=O R R' : + Nu: - C-O : - R R' Nu tetrahedral intermediate Nu-H C-O-H + Nu: - R R' Nu The typical reaction with carboxylic acids and their derivatives is nucleophilic substitution . The first step is nucleophilic addition to give the tetrahedral intermediate, but the presence of a good leaving group at the carbon center results in a cleavage reaction and regeneration of the carbonyl group.
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Nucleophilic Substitution at Acyl Carbon C=O R : + Nu: - X nucleophilic addition C-O : - R Nu tetrahedral intermediate X C-O : - R Nu X cleavage C=O R Nu + X: - This basic mechanism occurs in biological systems and is called an acyl transfer reaction .
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Example: Hydrolysis of an Acyl Chloride R-C- Cl :O: = + :O-H H : nucleophile nucleophilic addition R-C- Cl :O-H H + :O: - tetrahedral intermediate R-C- Cl :O-H H + :O: - - Cl - cleavage R-C-O-H :O: H + H 2 O R-C-O-H
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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Ch_322b_18.09 - Chapter 18.9 lecture note

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