Better nucleophiles accelerate an S N 2 reaction by increasing the degree of bonding in the transition state. This increased bonding stabilizes the transition state, thus lowering the activation energy and increasing the reaction rate. Steric hinderance slows the approach of the nucleophile, and thus reduced the reaction rate. When the carbon is tertiary, the steric hinderance is sufficient to stop the reaction entirely. Circle the most nucleophilic ion or molecule in each set.
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Each mechanism step shown below may contain a significant problem or error. Very briefly describe the error, then write the corrected version of the mechanism step. Try to keep your corrected version as close to the original as possible. Do not consider missing curved arrows or products. This addition cannot occur, because the carbon which gains the CN already has a full octet.