Question

Given below are two statements:
Statement (I): On nitration of m-xylene with \( \text{HNO}_3 \), \( \text{H}_2\text{SO}_4 \), followed by oxidation, 4-nitrobenzene-1, 3-dicarboxylic acid is obtained as the major product.
Statement (II): CH\(_3\) group is o/p-directing while NO\(_2\) group is m-directing group.
In the light of the above statements, choose the correct answer from the options given below:

• A. Statement I is false but Statement II is true
• B. Statement I is false but Statement II is true
• C. Both Statement I and Statement II are true
• D. Statement I is true but Statement II is false

Hint:

The methyl group (CH\(_3\)) is an electron-donating group that activates the aromatic ring towards electrophilic substitution at the o/p-positions. The nitro group (NO\(_2\)) is an electron-withdrawing group that directs substitution to the meta-position.

Answer 1

The Correct Option is C

- Statement (I): The nitration of m-xylene with \( \text{HNO}_3 \) and \( \text{H}_2\text{SO}_4 \) followed by oxidation indeed gives 4-nitrobenzene-1,3-dicarboxylic acid as the major product. This statement is correct. 
- Statement (II): The methyl group (CH\(_3\)) is o/p-directing, meaning it directs electrophilic substitution reactions to the ortho and para positions. The nitro group (NO\(_2\)) is m-directing, meaning it directs electrophilic substitution to the meta position. This is also correct. 
Therefore, both statements are true.

Answer 2

Step 1: Understand the statements.
Statement (I): On nitration of m-xylene with \( \text{HNO}_3 \) and \( \text{H}_2\text{SO}_4 \), followed by oxidation, 4-nitrobenzene-1,3-dicarboxylic acid is obtained as the major product.
Statement (II): The –CH₃ group is an ortho/para-directing group, while the –NO₂ group is a meta-directing group.

Step 2: Analyze Statement (I).
m-Xylene is 1,3-dimethylbenzene. When it undergoes nitration using concentrated \( \text{HNO}_3 \) and \( \text{H}_2\text{SO}_4 \), the nitro group (\( \text{NO}_2 \)) enters the position that is ortho or para to one of the –CH₃ groups, taking into account the directing influence of both methyl substituents.
For m-xylene, the position 4 relative to one of the –CH₃ groups is the most favorable site for substitution, giving **4-nitro-m-xylene** as the major nitration product.

On oxidation (for example, using \( \text{KMnO}_4 \)), each –CH₃ group is converted into a –COOH group. Hence, the product obtained is **4-nitrobenzene-1,3-dicarboxylic acid**.
Therefore, Statement (I) is true.

Step 3: Analyze Statement (II).
The –CH₃ group is an electron-donating group that activates the benzene ring and directs incoming electrophiles to the **ortho and para positions**.
The –NO₂ group, on the other hand, is an electron-withdrawing group due to its –M (mesomeric) and –I (inductive) effects, and it directs incoming electrophiles to the **meta position**.
Hence, Statement (II) is also true.

Step 4: Conclusion.
Both statements are scientifically correct. Statement (I) describes the correct product formed in the reaction, and Statement (II) correctly explains the directive influence of the –CH₃ and –NO₂ groups.

Final Answer:
Both Statement I and Statement II are true.
\[ \boxed{\text{Both Statement I and Statement II are true.}} \]