Question:

1-Chloro-4-nitrobenzene, 1-Chloro-2,4-dinitrobenzene and 1-Chloro-2,4,6-trinitrobenzene are transformed to corresponding phenols with the reagents X, Y, Z respectively. What are X, Y, Z?

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More nitro groups on haloarenes = easier nucleophilic substitution due to increased stabilization of the intermediate.
Updated On: May 15, 2025
  • X = H\textsubscript{2}O; Y = NaOH, 365K; Z = NaOH, 445K
  • X = (i) NaOH, 443K (ii) H\textsuperscript{+}; Y = (i) NaOH, 368K (ii) H\textsuperscript{+}; Z = Warm H\textsubscript{2}O
  • X = (i) NaOH, 625K (ii) H\textsuperscript{+}; Y = (i) NaOH, 440K (ii) H\textsuperscript{+}; Z = H\textsubscript{2}O/H\textsuperscript{+}
  • X = NaOH, 625K; Y = H\textsubscript{2}O; Z = NaOH, 440K
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The Correct Option is B

Solution and Explanation

The reactivity of haloarenes towards nucleophilic substitution increases with the number of electron-withdrawing nitro groups.
- For 1-chloro-4-nitrobenzene, higher temperature and NaOH/H\textsuperscript{+} are required.
- 1-chloro-2,4-dinitrobenzene reacts at a slightly lower temperature.
- 1-chloro-2,4,6-trinitrobenzene is highly reactive and can be converted to phenol with just warm water.
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