Changes in Mechanism and Transition State Structure for Solvolysis Reactions of Ring Substituted Benzyl Chlorides in Aqueous Solution.

Rate and product data are reported for the solvolysis reactions of twenty-seven mono, di (3,4) and tri (3,4,5) ring-substituted benzyl chlorides. The first order rate constant for solvolysis in 20% acetonitrile in water decrease from = 2.2 s for 4-methoxybenzyl chloride to 1.