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JEE Chemistry 2023 Question with Solution

Compound B' is _____.

Reaction scheme showing a substituted phenol ring treated with sodium nitrite and hydrochloric acid to form A, then with ammonium hydrosulfide and water to form major product B.
  • A
    Benzene ring with methyl and isopropyl substituents, an amino group on one carbon and a hydroxyl group on another carbon.
  • B
    Benzene ring with methyl and isopropyl substituents only, without amino, hydroxyl, or thiol functional groups.
  • C
    Benzene ring with methyl and isopropyl substituents, a thiol group on one carbon and a hydroxyl group on another carbon.
  • D
    Benzene ring with methyl and isopropyl substituents and a thiol group attached, without any hydroxyl group.

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: The substrate shown is a substituted phenol. It is treated first with NaNO2\text{NaNO}_2 and HCl\text{HCl} to form A, and then A is treated with NH4SH\text{NH}_4\text{SH} and H2O\text{H}_2\text{O} to give major product B.

Find: The correct structure of compound B.

From the solution, the stated conclusion is that the correct option is C.

Therefore, the major product B corresponds to option C.

Source Discrepancy Note

The answer key says (1), which maps to A. However, the solution explicitly states:

The Correct Option is C\text{The Correct Option is C}

By the answer-resolution rule, the solution is treated. Hence the final answer is C.

Common mistakes

  • Choosing the option from the answer key key without checking the solution is incorrect here because the source contains a mismatch. Use the solution when they disagree.

  • Ignoring the functional groups drawn in the options is a mistake. Compare whether the product retains the OH group and whether the new substituent is NH$$$_2$$ or SH before selecting the structure.

  • Selecting a structure only on the basis of the ring skeleton is wrong because all options have similar substituted aromatic frameworks. Match the exact substitution pattern shown in the final product option.

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