Cleavage of (2-hydroxy- and 2-alkoxycycloalkyl)mercuric chlorides by hydrochloric acid

Abstract

The kinetics of the cleavage of ( trans-2-methoxycyclohexyl)-, ( trans-2-ethoxycyclohexyl)-, ( trans-2-hydroxycyclohexyl)-, and ( trans-2-methoxycyclopentyl)mercuric chlorides by hydrochloric acid have been investigated by a conductivity method. The reaction in alcohol/water mixtures were found to be pseudo-second-order. The enthalpies and entropies are discussed in relation to the nature of the organic radical. A tentative mechanism for the reaction is proposed which involves a rapid and reversible addition of a proton to the (2-alkoxycycloalkyl)mercuric chloride with subsequent formation of the cycloalkene and mercuric chloride.