Editing Amide (section)

===Hydrolysis===
Amides hydrolyse in hot [[alkali]] as well as in strong [[acid]]ic conditions. Acidic conditions yield the carboxylic acid and the ammonium ion while basic hydrolysis yield the carboxylate ion and ammonia. The protonation of the initially generated amine under acidic conditions and the deprotonation of the initially generated carboxylic acid under basic conditions render these processes non-catalytic and irreversible. Electrophiles other than protons react with the [[carbonyl]] oxygen. This step often precedes hydrolysis, which is catalyzed by both [[Brønsted acid]]s and [[Lewis acid]]s. [[Peptidase]] enzymes and some synthetic catalysts often operate by attachment of electrophiles to the carbonyl oxygen.

{| class="wikitable sortable"
!Reaction name !! Product !! class="unsortable" | Comment
|-
| Dehydration
|Nitrile
| Reagent: [[phosphorus pentoxide]]; [[benzenesulfonyl chloride]]; [[TFAA]]/[[pyridine|py]]<ref>{{US patent|5935953}}</ref>
|-
| [[Hofmann rearrangement]]
|Amine with one fewer carbon atom
|Reagents: [[bromine]] and [[sodium hydroxide]]
|-
| [[Amide reduction]]
| Amines, aldehydes
|Reagent: [[lithium aluminium hydride]] followed by hydrolysis
|-
|[[Vilsmeier–Haack reaction]]
|[[Aldehyde]] (via [[imine]])
| [[Phosphoryl chloride|{{chem2|POCl3}}]], aromatic substrate, formamide
|-
|[[Bischler–Napieralski reaction]]
|Cyclic aryl [[imine]]
| [[Phosphoryl chloride|{{chem2|POCl3}}]], [[thionyl chloride|{{chem2|SOCl2}}]], etc.
|-
|[[Darzens reaction|Tautomeric chlorination]]||[[Imidoyl chloride]]||[[Oxophilic]] halogenating agents, e.g. [[Phosgene|COCl<sub>2</sub>]] or [[Thionyl chloride|SOCl<sub>2</sub>]]
|}