Amide

An amide, also known as an acid amide, is a compound with the functional group R_nE(O)_xNR'₂ (R and R' refer to H or organic groups).

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• The amides are the least reactive of the carboxylic acid derivatives, in part because they are strongly stabilized by delocalization of the nitrogen lone pair (...) As a consequence, their nucleophilic addition – eliminations require relatively harsh conditions. For example, hydrolysis to the corresponding carboxylic acid occurs only upon prolonged heating in strong aqueous acid or base by addition – elimination mechanisms. Acid hydrolysis liberates the amine in the form of an ammonium salt.
  • K. Peter C. Vollhardt, Neil E. Schore (2011) Organic chemistry : structure and function 6th ed. Ch. 20 : Carboxylic Acid Derivatives

• In contrast to carboxylic acids and esters, the reaction of amides with lithium aluminum hydride produces amines instead of alcohols. (...) The mechanism of reduction begins with hydride addition, which gives a tetrahedral intermediate. Elimination of an aluminum alkoxide leads to an iminium ion.Addition of a second hydride gives the final amine product. (...) Reduction of amides by bis(2-methylpropyl)aluminum hydride (diisobutylaluminum hydride) furnishes aldehydes.
  • K. Peter C. Vollhardt, Neil E. Schore (2011) Organic chemistry : structure and function 6th ed. Ch. 20 : Carboxylic Acid Derivatives

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Amide