Nucleophilic Substitution Reaction of p-Nitrobenzyl Chloroformate

Abstract

The solvolysis of p-nitrobenzyl chloroformate in all the solvents studied and the methanolysis of the substrate in acetone give no evidence for mechanistic change. This substrate, where bond making is more progressed by a dominant addition-elimination pathway in which the rate determining step involves nucleophilic addition. These pathway are assisted by generral-base catalysis, either by a second methanol molecule or by an acetone solvent molecule. The second-order kinetics pathway can represent nucleophilic attack by methanol without general-base catalysis.