Question

Can anyone explain the reaction mechanism below with a diagram of the movement of electrons?

Answer 1

How about this?

Explanation:

Step 1. Nucleophilic substitution

The reaction is base-catalyzed, so the nucleophile is the naphthoxide ion. I will use `"R"` to represent the α-naphthyl group.

The α-naphthoxide ion attacks the less-substituted substituted carbon atom of the oxirane ring to form an alkoxide ion.

The new ion, in turn, attacks the carbon adjacent to the `"Cl"` in a second `"S"_text(N)2` displacement to form a new oxirane.

Step 2. Nucleophilic substitution

The isopropylamine attacks the less substituted carbon atom of the oxirane ring.

During workup, the oxide and ammonium ions become protonated/deprotonated to give the amino alcohol.