The order of decreasing reactivity towards an electrophilic reagent, for the following would be (i) benzene (ii) toluene (iii) chlorobenzene (iv) phenol
- (ii) > (iv) > (i) > (iii)
- (iv) > (iii) > (ii) > (i)
- (iv) > (ii) > (i) > (iii)
- (i) > (ii) > (iii) > (iv)
Answer
(3) (iv) > (ii) > (i) > (iii)
Solution
As per NCERT, groups that increase the electron density of the ring activate it towards electrophilic substitution.
Phenol: –OH shows a strong +R effect ⇒ ring strongly activated.
Toluene: –CH3 shows +I effect and hyperconjugation ⇒ ring activated, but less than by –OH.
Benzene: no substituent (reference).
Chlorobenzene: –I effect of Cl is stronger than its +R effect ⇒ ring deactivated.
∴ Decreasing reactivity: phenol > toluene > benzene > chlorobenzene, i.e. (iv) > (ii) > (i) > (iii)
Answer: (3)