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Reactivity Documentation

Metals, Alkali, Very Active

mixed with

Hydrocarbons, Aromatic

Summary

Details

Metals, Alkali, Very Active is a reactive group.
Hydrocarbons, Aromatic is a reactive group.

Reactivity Predictions (for each pair of reactive groups)

Hydrocarbons, Aromatic mixed with
Metals, Alkali, Very Active

Hazard Predictions

Solid sodium metal does not react with aromatic hydrocarbons (Pascal, P. 1966. Nouveau Traité de Chimie Minérale. Vol. 2, Part 1, p. 224. Masson et Cie.).

Alkali metals do not react with benzene, toluene, or xylene in the absence of proton sources (such as water, alcohols, or ammonium salts) (E. M. Kaiser, Synthesis, 1972, (8), p. 391-415; C. B. Wooster, K. L. Godfrey, J. Am. Chem. Soc., 1937, (59), p 596-597).

Alkali metals dissolved in ammonia perform stepwise one-electron reductions of aromatic hydrocarbons in the presence of proton sources (inc. alcohols, water, or ammonium salts). The reaction produces 1,4-cyclohexadienes (Birch reduction) or cyclohexenes (Benkeser reduction) (A. A. Akhrem, I. G. Reshetova, Y. A. Titov: Birch Reductions of Aromatic Compounds, IFI/Plenum, New York, 1972; E. M. Kaiser, Synthesis, 1972, (8), p. 391-415).