The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH,

Question:

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.

Solution:

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.

Leave a comment

Close

Click here to get exam-ready with eSaral

For making your preparation journey smoother of JEE, NEET and Class 8 to 10, grab our app now.

Download Now