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. 


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.

R-Cl+KOH(aq) R-OH+ KCl
Alkyl                         Alcohol
chloride

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.

R-CβH2-CαH2-Cl+KOH(alc) R-CH=CH2+ KCl+ H2O
Alkyl chloride                                       Alkene

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.