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

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1 Answer
May 12, 2018

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.

Step 1

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.

Step 2

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