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Naoh ethanol water h3o intermediates produced in reactions of alcohols with phosphorus tribromide and thionyl chloride last two examples are seldom isolated, and these reactions continue on to alkyl bromide and chloride products. A rigorous proof of the configurational inversion that occurs at the substitution site in S N 2 reactions makes use of such reactions. The resulting "onium" intermediate then loses a proton to a base, giving the substitution product. Indeed, for reversible reactions such as this the laws of thermodynamics require that the mechanism in both directions proceed by the same reaction path. This is known as naoh ethanol water h3o principle of microscopic reversibility.
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