Which of the following sequence of reactions is suitable to synthesize chlorobenzene?
- Benzene, Cl2, anhydrous FeCl3
- Phenol, NaNO2, HCl, CuCl
- [figure] , HCl
- [figure] , HCl, Heating
Answer
(1) Benzene, Cl2, anhydrous FeCl3
Solution
(1) As per NCERT, aryl chlorides are prepared by electrophilic substitution of arenes with chlorine in the presence of a Lewis acid:
C6H6 + Cl2 anhyd. FeCl3 C6H5Cl + HCl ⇒ suitable.
(2) Phenol has no -NH2 group, so NaNO2/HCl cannot form a diazonium salt; the C-OH bond of phenol is not replaced by Cl either.
(3) Benzene does not react with HCl.
(4) Aniline with HCl only forms the salt anilinium chloride, C6H5NH3+Cl- (chlorobenzene needs diazotisation and then CuCl/HCl, Sandmeyer reaction).
Answer: (1)