Question

Compound A when reacted with PCl₅ and then with ammonia gave B. B when treated with bromine and caustic potash produced C. C on treatment with HCl and NaNO₂ at 0°C and then boiling produced ortho-cresol. Compound A is 

(a) o-toluic acid 

(b) o-chlorotoluene 

(c) o-bromotoluene 

(d) m-toluic acid

Answer 1

(a) o-toluic acid 

Nature of reagents used during the reaction of C to form o-cresol indicates that at first C is diazotised to form diazonium salt which on boiling is converted to o-cresol. Thus C must be o-toluidine.