Elimination reactions of ions in the gas phase. IV—Comparative investigation of water elimination in odd and even electron hydroxyl cations of 6‐undecanol

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Abstract
Reactivity differences between odd ([M]+) and even electron ions (α‐cleavage product) were studied by comparing water elimination mechanisms in 6‐undecanol. The compounds specifically labelled with deuterium in positions 6, 5 + 7, 4 + 8 and 3 + 9 were made, and a detailed investigation of tghe metastable ion transitions carried out. A highly specific 1,4 elimination of water without preceding intramolecular hydrogen exchange occurs from [M]+, but equal amounts of 1,3 and 1,4 elimination of water preceded by specific hydrogen exchange between ‐OH and the hydrocarbon chain occurs from the α‐cleavage ion [M – C5H11]+. To make such distinctions a thorough examination of metastable ions is essential.