# Major product of mononitration of 3-methylphenol

From NCERT Class Chemistry Part 2:

Example 11.5

Write the structures of the major products expected from the following reactions:

(a) Mononitration of 3-methylphenol
(b) Dinitration of 3-methylphenol
(c) Mononitration of phenyl methanoate.

Solution

The combined influence of $$\ce{-OH}$$ and $$\ce{-CH3}$$ groups determine the position of the incoming group.

Since $$\ce{-OH}$$ and $$\ce{-CH3}$$ are o,p-directing groups, shouldn’t the major product be 3-methyl-2-nitrophenol? Why not?

• Weigh inductive, mesomeric and steric effects in the balance. – Sir Arthur7 Mar 6 '20 at 7:36
• @SirArthur7 I can’t seem to get the answer right,can you explain it in detail? – JjJot Mar 6 '20 at 8:14
• In order for a nitro- group to be attached to a phenyl group, you must have an H atom available next to this carbon atom. If NO2 wants to attack the Carbon number 2, there is no H atom on Carbon 1 or 3. So the reaction is not possible. – Maurice Mar 6 '20 at 8:51
• @Maurice why is this necessary – JjJot Mar 6 '20 at 15:32
• @Jashanjot : The nitration reaction is due to the ion $NO_2^+$ attrcte – Maurice Mar 7 '20 at 19:32