Consider the following compounds : [figure] Arrange these compounds in the increasing order of reactivity with nitrating mixture.
- c < b < a
- b < c < a
- c < a < b
- b < a < c
Answer
(4) b < a < c
Solution
Nitration (conc. HNO3 + conc. H2SO4) is an electrophilic substitution by NO2+; electron-releasing groups activate and electron-withdrawing groups deactivate the ring.
b (-NO2): strong –I and –R strongly deactivating, least reactive
a (–Cl): –I > +R weakly deactivating (o/p-directing)
c (-OCH3): +R > –I activating, most reactive
b < a < c
Answer: (4)