CAIE A-Level Chemistry 34.3.2 Hydrolysis and Reduction of Amides

Practise predicting products of acidic or alkaline amide hydrolysis and LiAlH₄ reduction.

Exam points

with aqueous acid, cleave the C–N bond to a carboxylic acid and a protonated amine or ammonium ion
with aqueous alkali, form a carboxylate ion and the corresponding amine or ammonia
use LiAlH4 to replace the amide C=O by CH2 and form an amine without losing the carbon skeleton

[Maximum number: 2]

Amino acids are molecules that contain $-\mathrm{NH}_{2}$ and -COOH functional groups.
Glycine, $\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH}$ , is the simplest stable amino acid.

Fig. 6.1 shows two syntheses starting with glycine.

Fig. 6.1

Draw the structure of the organic product U that forms when hippuric acid reacts with an excess of $\mathrm{LiAlH}_{4}$ in reaction 3 .

Figure for Answer to Question 34.3.2—Reactions of amides question 1 — CAIE A-Level Chemistry A2

- carboxylic acid to primary alcohol COOH to $\mathrm{CH}_{2} \mathrm{OH}$

- amide to amine CONH to $\mathrm{CH}_{2} \mathrm{NH}$

- rest of the molecule is correct (carbons and benzene ring) mark as •

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34.3.2—Reactions of amides question 1