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Question -

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



Answer -

In an aqueous solution, KOH almostcompletely ionizes to give OHтИТ┬аions. OHтИТ┬аionis a strong nucleophile, which leads the alkyl chloride to undergo asubstitution reaction to form alcohol.

On the other hand, an alcoholic solution ofKOH contains alkoxide (ROтИТ) ion, which is a strong base. Thus, it can abstract ahydrogen from the ╬▓-carbon of the alkyl chloride and form an alkene byeliminating a molecule of HCl.

OHтИТ┬аion is a muchweaker base than ROтИТ┬аion. Also, OHтИТ┬аion is highlysolvated in an aqueous solution and as a result, the basic character of OHтИТ┬аiondecreases. Therefore, it cannot abstract a hydrogen from the ╬▓-carbon.

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