Amides (Edexcel International A Level Chemistry)

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Amide Formation

  • Amides are organic compounds with an -CONR2 functional group
  • They can be prepared from the condensation reaction between an acyl chloride and ammonia or amine
  • In a condensation reaction, two organic molecules join together and in the process eliminate a small molecule
  • In this case, the acyl chlorides and ammonia or amine join together to form an amide and eliminate an HCl molecule

Condensation reaction

  • The chlorine atom in acyl chlorides is electronegative and draws electron density from the carbonyl carbon
  • The carbonyl carbon is therefore electron-deficient and can be attacked by nucleophiles
  • The nitrogen atom in ammonia and amines has a lone pair of electrons which can act as a nucleophile and attack the carbonyl carbon
  • As a result, the C-Cl bond is broken and an amide is formed
  • Whether the product is a substituted amide or not, depends on the nature of the nucleophile
    • Primary and secondary amines will give a substituted amide
    • The reaction of acyl chlorides with ammonia will produce a non-substituted amide

Acyl chlorides undergo condensation reactions with ammonia and amines to form amides

  • Note that ammonia is basic and the inorganic product is acidic, so there will be a reaction between the two molecules

NH3 + HCl → NH4Cl

  • We can therefore write the overall equation for the reaction of propanoyl chloride and ammonia as

CH3CH2COCl + 2NH3 → CH3CH2CONH2 + NH4Cl

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Sonny

Author: Sonny

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Sonny graduated from Imperial College London with a first-class degree in Biomedical Engineering. Turning from engineering to education, he has now been a science tutor working in the UK for several years. Sonny enjoys sharing his passion for science and producing engaging educational materials that help students reach their goals.