Edexcel A-Level Chemistry A2 19.3 Amines Are Miscible with Water As a Result of Hydrogen Bonding and the Reasons for the Difference in Basicity Between Questions

For solubility draw the hydrogen bond to water; for basicity compare how available the nitrogen lone pair is after alkyl donation or delocalisation into a ring.

Exam points

Draw hydrogen bonding between amines and water with lone pairs and dipoles.
Compare basicity of aliphatic amines, ammonia and phenylamine using lone-pair availability.
Explain phenylamine or caffeine weakness by nitrogen lone-pair delocalisation.

[Maximum number: 2]

The synthetic drugs of the 'Caine' family are used as local anaesthetics. Caine drugs prevent nerve activity by binding to sodium channel receptors in the lipid cell membranes of neurons.

benzocaine

procaine

lidocaine

articaine

Procaine can react with hydrochloric acid to form a monohydrochloride salt.

Explain by considering both nitrogen atoms in procaine which nitrogen is more likely to be protonated in the reaction with hydrochloric acid.

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Edexcel A-Level Chemistry A2 19.3 Amines Are Miscible with Water As a Result of Hydrogen Bonding and the Reasons for the Difference in Basicity Between Questions question 1