Question 12.2: What product would you expect from a nucleophilic substituti...

Organic Chemistry with Biological Applications

What product would you expect from a nucleophilic substitution reaction of
(R)-1-bromo-1-phenylethane with cyanide ion, $^{-}C \equiv N$ , as nucleophile? Show the stereochemistry of both reactant and product, assuming that inversion of configuration occurs.

Strategy

Draw the R enantiomer of the reactant, and then change the configuration of the chirality center while replacing the –Br with a –CN.

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