JEE Chemistry 2025 Question with Solution

Given: Two statements about nitration of $m$-xylene and directing effects of $CH_3$ and $NO_2$ groups.

Find: Which option correctly evaluates Statement (I) and Statement (II).

From the solution, Statement (I) is correct because nitration of $m$-xylene with

$$\text{HNO}_3 / \text{H}_2\text{SO}_4$$

gives the major nitration product at the favorable position directed by the methyl groups, forming $4$-nitro-$m$-xylene. On oxidation, both methyl groups are converted into carboxylic acid groups, so the product becomes

$$4\text{-nitrobenzene-}1,3\text{-dicarboxylic acid}$$

Therefore, Statement (I) is true.

Also, Statement (II) is correct. The $CH_3$ group is an electron-donating group and is ortho/para-directing, whereas the $NO_2$ group is an electron-withdrawing group and is meta-directing.

Hence, both statements are true.

The correct option is C.

Given:

• Statement (I): On nitration of $m$-xylene with $HNO_3$ and $H_2SO_4$, followed by oxidation, $4$-nitrobenzene-$1,3$-dicarboxylic acid is obtained as the major product.
• Statement (II): $CH_3$ is ortho/para-directing while $NO_2$ is meta-directing.

Find: Determine the truth values of both statements.

Step 1: Understand Statement (I).

$m$-xylene is $1,3$-dimethylbenzene. During nitration using concentrated

$$\text{HNO}_3 \text{ and } \text{H}_2\text{SO}_4$$

the incoming $NO_2$ group enters the position favored by the directing influence of the methyl groups.

The major nitration product is $4$-nitro-$m$-xylene.

Step 2: Oxidation step.

On oxidation, each $CH_3$ side chain is converted into $COOH$. Therefore, the product becomes

$$4\text{-nitrobenzene-}1,3\text{-dicarboxylic acid}$$

So Statement (I) is true.

Step 3: Understand Statement (II).

The $CH_3$ group donates electron density to the ring and directs electrophilic substitution to the ortho and para positions.

The $NO_2$ group withdraws electron density by $-I$ and $-M$ effects and directs substitution to the meta position.

So Statement (II) is also true.

Conclusion: Both statements are true. Therefore, the correct option is C.