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

Practise Edexcel IAL Chemistry 19.3 by drawing hydrogen bonds to water and comparing amine basicity through lone-pair availability, alkyl donation and aromatic delocalisation.

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