The compound `C_(7)H_(8)` undergoes the following reactions :
`C_(7)H_(8) overset(3Cl_(2)//Delta)to Aoverset(Br_(2)//Fe)toB overset(Zn//HCl)toC`
The product 'C' is

Options

A. 3-bromo-2,4,6-trichlorotoluene
B. o-bromotoluene
C. m-bromotoluene
D. p-bromotoluene

Answer

C

Explanation

Given,
`C_(7)H_(8)overset(3Cl_(2)//Delta)to A overset(Br_(2)//Fe)to B overset(Zn//HCl)to C`
The reaction in the above road map can be explained by the following steps.
Step I Toluene (A) undergoes side chain halogenation with excess of chlorine to give benzotrichloride (A).

Step II In compound (A), the substituent `C Cl_(3)` is an electron withdrawing group, so the electrophile will attack at m-position. Thus, benzotrichloride reacts with bromine in presence of Fe-catalyst to give m-bromobenzotrichloride (B).

Step III m-bromobenzotrichloride undergoes reduction with Zn in presence of HCl to give m-bromotoluene (C ).