Chemistry A2 · Nitrogen compounds. The idea in plain words, the rules to remember, the mistake to avoid and a worked example, written and checked by Mega Lecture.
An amide contains the group –CONH2, or –CONHR if one hydrogen on the nitrogen is replaced. Amides are made at room temperature from an acyl chloride with ammonia or with a primary amine.
Hydrolysis breaks the C–N bond. Heating with aqueous acid gives the carboxylic acid and an ammonium (or amine) salt. Heating with aqueous alkali gives the salt of the carboxylic acid and ammonia (or the amine). Reduction with LiAlH4 changes C=O into CH2 and gives an amine.
Amides are much weaker bases than amines. The lone pair on nitrogen is delocalised into the C=O group, pulled by the electronegative oxygen, so it is not available to accept H+. Amides are neutral in water.
Students mix up hydrolysis and reduction. Hydrolysis splits the molecule at the C–N bond into two parts. Reduction with LiAlH4 keeps the C–N bond and every carbon atom; only C=O becomes CH2.
Answer: Sodium ethanoate and propylamine (propan-1-amine)
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