Chapter 15, Problem 44P

Interpretation Introduction

Interpretation:

The product formed in the given reaction is to be predicted, and the reason for the formation of this product is to be explained.

Concept Introduction:

Aryl halides undergo nucleophilic substitution reactions in the presence of strong base, $:N{H}_2^{-}$ in liquid ammonia through an elimination-addition mechanism. This mechanism involves the formation of a highly unstable intermediate called benzyne.

Activating groups like alkyl groups gives substitution at the ortho and para position. Because they increase the electron densities at the ortho and para due to the delocalization of pi electrons of benzene ring. Ortho and para sites of the benzene ring is highly electron rich and thus electrophile usually attacks on these sites.