Nucleophilic acyl substitution
For a carboxylic acid derivative, nucleophilic addition can form a tetrahedral intermediate whose collapse expels a leaving group and restores the carbonyl.
Key knowledge
For a carboxylic acid derivative, nucleophilic addition can form a tetrahedral intermediate whose collapse expels a leaving group and restores the carbonyl. The net result replaces an acyl substituent. Leaving-group ability and resonance donation influence relative reactivity of acid derivatives.
Conditions and scope
- Acid/base catalysis and proton transfers change the detailed sequence.
- The addition–elimination model applies within its stated regime; not every acyl transfer has a long-lived tetrahedral intermediate.
Sources · 1
References
Sources retain their recorded scope. A source link alone does not establish verification of every statement.
Evidence and review
Inspected addition/elimination mechanism and carboxylic-acid-derivative comparison.
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Entry details
Permanent link to this entry ↗- Record identity
- uni-chem-acyl-substitution
- Revision
- core.1
- Structured reference record
- University core expansion