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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 ionizes to give OH− ions. OH− ion is a strong nucleophile, which leads the alkyl chloride to undergo a substitution reaction to form alcohol. On the other hand, an alcoholic solution of KOH contains alkoxide (RO−) ion, which is a strong...
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In an aqueous solution, KOH almost completely ionizes to give OH− ions. OH− ion is a strong nucleophile, which leads the alkyl chloride to undergo a substitution reaction to form alcohol. On the other hand, an alcoholic solution of KOH contains alkoxide (RO−) ion, which is a strong base. Thus, it can abstract a hydrogen from the β-carbon of the alkyl chloride and form an alkene by eliminating a molecule of HCl. OH− ion is a much weaker base than RO− ion. Also, OH− ion is highly solvated in an aqueous solution and as a result, the basic character of OH− ion decreases. Therefore, it cannot abstract a hydrogen from the β-carbon. read less
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