The kinetics of methanolysis (solvolysis) in 97.4% MeOH-dioxan of a series of 4'-substituted 4-benzyloxybenzyl chlorides, and of 4-anisy1, 4-phenoxybenzy1, and benzyl chlorides have been studied and discussed, including comparisons with the data for the corresponding series of benzoyl chlorides, previously reported by us. The 4'substituted precursor alcohols, chlorides, and product methyl ethers are all new compounds. 4-Anisyl chloride and the series of benzyloxybenzyl chlorides react by the S, 1 mechanism, whereas benzyl chloride reacts by the S,2 mechanism. 4-Phenoxybenzyl chloride shows intermediate behaviour. A similar pattern was observed with the corresponding benzoyl compounds. In both series the reactivity order is CH,O > 4'-CH,C,H4CH,0 (-0.76) >C,H5CH,0 (-0.74) 7 4'-CIC,H4CH20 (-0.69) > 4'-N02C,H4CH,0 (-0.60) > C6H50 > H (values in parentheses are new IS+ values). At 25" the overall range of rates is 4 290 in the benzyl series, compared with only 2.42 in the benzyl series. The Arrhenius parameters in the two series demonstrate, however, an underlying simil
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