Question

Question: What neutral nucleophile is needed to convert dihalide A to ticlopidine, an antiplatelet drug used to reduce the risk of strokes?

Short answer

The structure of the neutral nucleophile is shown below:

Step-by-step solution

Nucleophilic substitution reaction

A nucleophilic substitution reaction is similar to an acid-base reaction. In this reaction, the nucleophile acts as a base and donates electrons to the electrophile.

Reaction of Lewis base and Lewis acid

The complete reaction is shown below:

Attack of the nucleophile on the electrophile

In the above reaction, the lone pair of N (Lewis base) donates its electron pair to the electrophilic carbon atom of 1-chloro-2-(chloromethyl)benzene (Lewis acid). This leads to the removal of the chlorine group.

After that, the proton is transferred to form ticlopidine. Thus, the structure of the neutral nucleophile is shown below:

Structure of nucleophile