REARRANGEMENT REACTIONS FOLLOWING ELECTRON IMPACT ON ETHYL AND ISOPROPYL ESTERS

Abstract

The mass spectra of ethyl and isopropyl propionate and butyrate show rearrangement ions R₁COOH⁺ and R₁C(OH)₂⁺ formed by reactions [a] and [b]:[Formula: see text]The mass spectra of ethyl-d₂ propionate and butyrate show that both [a] and [b] occur with essentially complete scrambling of the alkoxy hydrogens. For the isopropyl esters the mass spectra of the isopropyl-d₆ molecules show that reaction [a] occurs by transfer of one of the methyl hydrogens to the acid moiety while reaction [b] occurs predominately by transfer of two methyl hydrogens.