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  • https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/08%3A_Nucleophilic_Substitution_and_Elimination_Reactions/8.05%3A_Mechanisms_of_Nucleophilic_Substitution_Reactions
    Two simple mechanisms can be written for the reaction of chloromethane with hydroxide ion in aqueous solution that differ in the timing of bond breaking relative to bond making. In the first mechanism...Two simple mechanisms can be written for the reaction of chloromethane with hydroxide ion in aqueous solution that differ in the timing of bond breaking relative to bond making. In the first mechanism, A , the overall reaction is the result of two steps, the first of which involves a slow dissociation of chloromethane to solvated methyl carbocation and solvated chloride ion. The second step involves a fast reaction between the carbocation and hydroxide ion (or water) to yield methanol.

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