Amide

any derivative of an oxoacid in which an acidic hydroxy group has been replaced by an amino or substituted amino group

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

QuotesEdit

  • 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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