Predict the major product for the following reaction.

Question

Quizplus · Accepted Answer

The reaction involves an Sn2 mechanism, where the nucleophile (cyanide) attacks the electrophilic carbon of the alkyl halide (1-bromo-3-methylbutane) and replaces the leaving group (bromine). This results in the formation of a new carbon-cyanide bond and a breaking of the carbon-bromine bond. The product formed will therefore be the one where the nucleophile attacks the primary carbon (which has a smaller steric hindrance relative to the tertiary carbon) and forms a linear alkyl cyanide (II). The other products (I, III, and IV) are either not formed or are formed to a lesser extent due to steric hindrance or unfavorable bond angles.

Predict the Major Product for the Following Reaction