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