Question

The polarity of C – X bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of – OH group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution of arenes. Nucleophilic substitution reactions are categorised into SN1 and SN2 on the basis of their kinetic properties. Chirality has a profound role in understanding the SN1 and SN2 mechanism.

Account for the following :

What happens when chlorobenzene and methyl chloride are treated with sodium metal in dry ether ?

Which reagents are required for one step conversion of chlorobenzene to toluene ?