Question

Among the following, which will have inversion of configuration on reaction with aqueous alkali and why?
(i) 1-chloropropane
(ii) 2-chloro-2-methylpropane

Hint:

Inversion of configuration typically occurs in SN2 reactions, where the attack is backside to the leaving group.

Answer 1

The inversion of configuration occurs in nucleophilic substitution reactions (SN2) where the nucleophile attacks the carbon opposite to the leaving group, causing the configuration to invert.
1-chloropropane will undergo inversion of configuration, as it undergoes an SN2 mechanism. However, 2-chloro-2-methylpropane, being a bulky tertiary substrate, undergoes an SN1 mechanism, where inversion may or may not occur.