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Basics of Organic Chemistry question

2025 · 29 Jan · Shift 2 · Q1
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Basics of Organic Chemistry question

2025 · 29 Jan · Shift 2 · Q1

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Given below are two statements : Statement (I): On nitration of m-xylene with HNO3,H2SO4\mathrm{HNO}_3, \mathrm{H}_2 \mathrm{SO}_4HNO3​,H2​SO4​ followed by oxidation, 4-nitrobenzene-1,3-dicarboxylic acid is obtained as the major product. Statement (II) : −CH3-\mathrm{CH}_3−CH3​ group is o/p-directing while −NO2-\mathrm{NO}_2−NO2​ group is m-directing group. In the light of the above statements, choose the correct answer from the options given below :
  1. A
    Statement I is true but Statement II is false
  2. B
    Both Statement I and Statement II are true
  3. C
    Both Statement I and Statement II are false
  4. D
    Statement I is false but Statement II is true
View written solutionFree

Correct answer: B

  1. Analyze Statement (II) first

    We know the directing effects in electrophilic aromatic substitution:

    • −CH3-\mathrm{CH_3}−CH3​ is an electron-donating group by hyperconjugation and inductive effect, so it is ortho/para-directing.
    • −NO2-\mathrm{NO_2}−NO2​ is a strong electron-withdrawing group, so it is meta-directing.

    Therefore, Statement (II) is true.

  2. Now analyze Statement (I)

    The substrate is m-xylene, i.e. 1,31,31,3-dimethylbenzene.

    Its structure has methyl groups at positions 1 and 3:

    C6H4(CH3)2\mathrm{C_6H_4(CH_3)_2}C6​H4​(CH3​)2​

    We now nitrate it using HNO3/H2SO4\mathrm{HNO_3/H_2SO_4}HNO3​/H2​SO4​.

  3. Directing effects during nitration

    Each −CH3-\mathrm{CH_3}−CH3​ group is ortho/para-directing.

    For m-xylene, possible nitration positions are 2, 4, 5, and 6.

    • Position 2: ortho to both methyl groups → sterically crowded
    • Position 4: para to one methyl and ortho to the other
    • Position 6: similar to position 2 by symmetry considerations
    • Position 5: meta to one methyl and ortho/para relation less favored overall

    The major nitration product is formed at position 4, giving 4-nitro-m-xylene (equivalently 2-nitro-1,3-dimethylbenzene depending on numbering convention).

  4. Oxidation step

    Strong oxidation converts each benzylic −CH3-\mathrm{CH_3}−CH3​ group into −COOH-\mathrm{COOH}−COOH.

    So:

    4-nitro-1,3-dimethylbenzene→oxidation4-nitrobenzene-1,3-dicarboxylic acid\text{4-nitro-1,3-dimethylbenzene} \xrightarrow[\text{oxidation}]{} \text{4-nitrobenzene-1,3-dicarboxylic acid}4-nitro-1,3-dimethylbenzeneoxidation​4-nitrobenzene-1,3-dicarboxylic acid

    Hence, Statement (I) is also true.

  5. Conclusion

    • Statement (I): True
    • Statement (II): True

    Therefore, the correct option is:

    B\boxed{\text{B}}B​

  6. Comparison with stored correct answer

    Stored correct answer = B

    Our derived answer = B

    So, they agree.

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