Practice problem 21.82 nitriles undergo alkylation at the α position much like ketones undergo alkylation at the α position. the α position of the nitrile is first deprotonated to give a resonance-stabilized anion (like an enolate), which then functions as a nucleophile to attack the alkyl halide. draw the mechanism described above for the transformation below (propyl chloride will be the rx in this reaction).