JEE MAIN - Chemistry (2025 - 29th January Evening Shift - No. 1)
Given below are two statements :
Statement (I): On nitration of m-xylene with $\mathrm{HNO}_3, \mathrm{H}_2 \mathrm{SO}_4$ followed by oxidation, 4-nitrobenzene-1,3-dicarboxylic acid is obtained as the major product.
Statement (II) : $-\mathrm{CH}_3$ group is o/p-directing while $-\mathrm{NO}_2$ group is m-directing group.
In the light of the above statements, choose the correct answer from the options given below :
Explanation
Statement I : Correct
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Nitration of m-xylene follows electrophilic aromatic substitution mechanism. First step is the generation of electrophile NO$_2^+$ (nitronium ion) and then the electrophile attacks the benzene ring. Methyl groups are ortho-para directing groups. The NO$_2^+$ in ortho position is not possible in this case due to the two neighbouring methyl groups. The nitro group is bonded to the para-position.
On oxidation, the methyl groups get converted to carboxylic acid groups. ($-$CH$_3$) to $-$COOH conversion). So, the statement is correct.
Statement II : Correct
$-$CH$_3$ group (methyl group) is ortho-para directing and $-$NO$_2$ group (nitro group) is meta directing.
$-$CH$_3$ group $\longrightarrow$ electron donating group
$-$NO$_2$ group $\longrightarrow$ electron withdrawing group.
Electron donating groups push electrons towards the ring and increase electron density. Electron donating groups give ortho-para directing products. Electron withdrawing groups pull electrons away from the ring and decrease electron density. Electron withdrawing groups give meta-directing products. So, the statement is correct.
So, both statement I and statement II are true.
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