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Chemistry · Glossary

What is Nucleophilic acyl substitution?

Also known as: tetrahedral intermediate

Definition 24.3 University Chemistry — Year 2 · Chapter 24 — Carboxylic Acid Derivatives

A nucleophilic acyl substitution replaces the group Z of an acyl compound by a nucleophile. It proceeds by addition of the nucleophile to the carbonyl carbon, giving a tetrahedral intermediate, followed by elimination of the leaving group, which restores the C=O\ce{C=O} bond.

Saponification of an ester. Hydroxide adds to the carbonyl carbon, giving the tetrahedral intermediate; the alkoxide leaves and the C=O bond reforms; the alkoxide, a strong base, then takes the proton of the acid. This last step makes the reaction complete. Saponification of an ester. Hydroxide adds to the carbonyl carbon, giving the tetrahedral intermediate; the alkoxide leaves and the C=O bond reforms; the alkoxide, a strong base, then takes the proton of the acid. This last step makes the reaction complete.
Saponification of an ester. Hydroxide adds to the carbonyl carbon, giving the tetrahedral intermediate; the alkoxide leaves and the C=O\ce{C=O} bond reforms; the alkoxide, a strong base, then takes the proton of the acid. This last step makes the reaction complete.
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