Abstract
The effect of o-, m-, and p-t-butyl and phenyl groups on solvolysis of the benzyl chlorides in 80% by volume ethanol–water was studied through conductometric rates and activation parameters. The rate constants for para-and meta-substituents were correlated by a Brown σ+ plot indicative of an SN1-type mechanism. Variations in ΔS* can be rationalized in terms of differential solvation effects. Solvolysis data for the trialkylbenzyl chlorides-2,4,6-trimethyl-, 2,4,6-tri-i-propyl-, 2,4-di-t-butyl-6-methyl-, and 2,4,6-tri-t-butylbenzyl chloride indicated an unexpected high reactivity for the latter compound. The abrupt increase in ΔS* for this compound is attributed to steric hindrance to solvation at the reaction site and steric acceleration is offered as an explanation for the unusual reactivity of this compound.
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