The compound C7H8 undergoes the following reactions : C7H8 3Cl2/ A Br2/Fe B Zn/HCl C The product 'C' is
- m-bromotoluene
- o-bromotoluene
- 3-bromo-2,4,6-trichlorotoluene
- p-bromotoluene
Answer
(1) m-bromotoluene
Solution
C7H8 is toluene.
⇒ 3Cl2/ (side-chain chlorination) gives benzotrichloride, A = C6H5CCl3.
⇒ -CCl3 is strongly electron-withdrawing, so it is meta-directing: Br2/Fe gives m-bromobenzotrichloride (B).
⇒ Zn/HCl reduces -CCl3 to -CH3, giving m-bromotoluene (C).
[figure]
Answer: (1)