Question

The displacement of a bromine atom by an amine is a substituion reaction. Write out the mechanism of this reaction (2-->3) Why might you expect that the reaction you have performed, using t-BuNH2, to be much slower than the same reaction using methylamine

Answer 1

Answer:

An alkyl halide can undergo SN2 reaction with an amine

Explanation:

The displacement of a bromine atom by an an amine (step 2---> 3) in the reaction sequence is an example of an SN2 reaction in which the amine is the nucleophile.

The nitrogen atom of the amine which bears a lone pair of electrons functions as the nucleophile and attacks the electrophilic carbon atom of the alkyl halide displacing the bromide and creating a new Carbon-Nitrogen bond. An ammonium intermediate is immediately formed and the reaction is completed by the abstraction of a hydrogen by a base (such as excess amine present in the system).

This reaction is slower with t-BuNH2 because of steric hindrance and steric crowding in the transition state. SN2 reactions are faster with methylamine where the alkyl carbon is easily accessible.

The detailed mechanism of this reaction has been attached to this answer.