Amide Reactions
Amides undergo many chemical reactions, usually through an attack on the carbonyl breaking the carbonyl double bond and forming a tetrahedral intermediate. Thiols, hydroxyls and amines are all known to serve as nucleophiles. Owing to their resonance stabilization, amides are less reactive under physiological conditions than esters. Enzymes, e.g. peptidases or artificial catalysts, are known to accelerate the hydrolysis reactions. They can be hydrolysed in hot alkali, as well as in strong acidic conditions. Acidic conditions yield the carboxylic acid and the ammonium ion while basic hydrolysis yield the carboxylate ion and ammonia. Amides are also versatile precursors to many other functional groups.
| Reaction name | Product | Comment |
|---|---|---|
| dehydration | nitrile | reagent: phosphorus pentoxide |
| Hofmann rearrangement | amine with one fewer carbon atoms | reagents: bromine and sodium hydroxide |
| amide reduction | amine | reagent: lithium aluminium hydride |
| Vilsmeier-Haack reaction | imine | POCl3, aromatic substrate, formamide |
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