10.22 What happens when

(i) n-butyl chloride is treated with alcoholic KOH,

(ii) bromobenzene is treated with Mg in the presence of dry ether,

(iii) chlorobenzene is subjected to hydrolysis,

(iv) ethyl chloride is treated with aqueous KOH,

(v) methyl bromide is treated with sodium in the presence of dry ether,

(vi) methyl chloride is treated with KCN?


(i) When n−butyl chloride is treated with alcoholic KOH, the formation of but−l−ene
takes place. This reaction is a dehydrohalogenation reaction.
CH3-CH2-CH2-CH2-Cl(Dehy drohalogenation)KOH(alc)
n-Butl chloride
                       CH3-CH2-CH2=CH2+KCl+H2O
                               But-l-ene
(ii) When bromobenzene is treated with Mg in the presence of dry ether,
phenylmagnesium bromide is formed.
(iii) Chlorobenzene does not undergo hydrolysis under normal conditions. However, it
undergoes hydrolysis when heated in an aqueous sodium hydroxide solution at a
temperature of 623 K and a pressure of 300 atm to form phenol.
(iv) When ethyl chloride is treated with aqueous KOH, it undergoes hydrolysis to form
ethanol.
CH3-CH2Cl(Hydrolysis)KOH(aq) CH3-CH2-OH+KCl
Ethyl chloride                           Ethanol 
(v) When methyl bromide is treated with sodium in the presence of dry ether, ethane
is formed. This reaction is known as the Wurtz reaction.
2CH3-Br+2Na(wurtz reaction)Dry ether CH3-CH3+2NaBr
(vi) When methyl chloride is treated with KCN, it undergoes a substitution reaction to
give methyl cyanide.
CH3-Cl+KCNNucleophilic substitution CH3-CN +KCl
Methylochloride                                   Methyl cyanide