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10.20    The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.

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In an aqueous solution, KOH almost completely dissociates into OH - ions. We know that OH - ions are strong nucleophile, which leads the alkyl chloride to undergo a reaction to form alcohol. But an alcoholic solution of KOH contains alkoxide (RO ) ion, which is a strong base. Thus, it can remove hydrogen from the β-carbon of the alkyl chloride and form an alkene.  The OH - ion is a weaker base than RO - ion. The basic character of OH - ion decreases in aqueous solution. Therefore, it cannot remove hydrogen from the β-carbon.

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Devendra Khairwa

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