1 - Chloro - 4 - nitrobenzene, 1 - Chloro - 2 , 4 - dinitrobenzene and 1 - Chloro - 2, 4, 6trinitrobenzene…

1 - Chloro - 4 - nitrobenzene, 1 - Chloro - 2 , 4 - dinitrobenzene and 1 - Chloro - 2, 4, 6trinitrobenzene are transformed to corresponding phenols with the reagents $\mathrm{X}, \mathrm{Y}, \mathrm{Z}$ respectively. What are $\mathrm{X}, \mathrm{Y}, \mathrm{Z}$ ?
  1. $\mathrm{X}=\mathrm{H}_2 \mathrm{O} ; \mathrm{Y}=\mathrm{NaOH}, 365 \mathrm{~K} ; \mathrm{Z}=\mathrm{NaOH}, 445 \mathrm{~K}$
  2. $\mathrm{X}=\text { (i) } \mathrm{NaOH}, 443 \mathrm{~K}, \mathrm{Y}=\text { (i) } \mathrm{NaOH}, 368 \mathrm{~K} \text {, }$ (ii) $\mathrm{H}^{+}$; (ii) $\mathrm{H}^{+}$; $\mathrm{Z}=\text { Warm } \mathrm{H}_2 \mathrm{O}$
  3. $\begin{array}{ll}\mathrm{X}=\text { (i) } \mathrm{NaOH}, 625 \mathrm{~K}, \mathrm{Y}=\text { (i) } \mathrm{NaOH}, 440 \mathrm{~K} \\ \text { (ii) } \mathrm{H}^{+} & \text {(ii) } \mathrm{H}^{+} \\ \mathrm{Z}=\mathrm{H}_2 \mathrm{O} / \mathrm{H}^{+} & \end{array}$
  4. $\mathrm{X}=\mathrm{NaOH}, 625 \mathrm{~K} ; \mathrm{Y}=\mathrm{H}_2 \mathrm{O} ; \mathrm{Z}=\mathrm{NaOH}, 440 \mathrm{~K}$

Solution


The reactivity of chlorobenzene increases with more$\mathrm{NO}_2$ groups and thus, nucleophilic substitution requires milder conditions.

Asked in: AP EAMCET 2023 (17 May Shift 1)

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