Electrophilic catalysis in solvolytic reactions—VI : Catalysed hydrolysis of 1-phenylalkyl chlorides

Abstract

The hydrolysis of four 1-phenylalkyl chlorides (CHPhAlkCl where Alk  Me, Et, i-Pr, t-Bu) in aqueous acetone and catalysed by HgCl 2 has been kinetically examined. The decrease in rate, as the series is ascended, is less in the presence than absence of the catalyst, particularly for the last two compounds. This is attributed to the operation of an additional inductomeric polarizability called into play by the catalyst. The mass-law effect, due to added chloride ions is significant only for 1-phenylethyl chloride, showing the importance of steric inhibition of resonance for the other three compounds.