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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.
Answers (1)
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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