Q20 / 180 · COMEDK 2023 (Evening Shift) · Chemistry

Identify the compounds A, B, C and D. $ \text { 1,2,2,2-tetrachloroethane } \xrightarrow[\Delta]{\mathrm{Zn}}[\mathrm{A}] $ [A] $ \xrightarrow[675 \mathrm{~K}]{\text { Fe tube }} $ [B] $ \xrightarrow[\text { Conc. } \mathrm{H}_2 \mathrm{SO}_4]{\text { Conc. } \mathrm{HNO}_3} $ [C] $ \xrightarrow[\text { Anhydrous } \mathrm{AlCl}_3]{\mathrm{Cl} /}$ [D]

  • A
    Figure
  • B
    Figure
  • C
    Figure
  • Correct answer
    D
    Figure

Solution

The reaction sequence is as follows:

1. Dehalogenation of 1,1,2,2-tetrachloroethane with Zn dust:
CHCl$_{2}$-CHCl$_{2}$ + 2Zn $\rightarrow$ CH$\equiv$CH + 2ZnCl$_{2}$. Thus, [A] is C$_{2}$H$_{2}$ (acetylene).

2. Cyclic polymerization of acetylene:
3C$_{2}$H$_{2}$ $\xrightarrow[675 \text{ K}]{\text{Fe tube}}$ C$_{6}$H$_{6}$ (benzene). Thus, [B] is benzene.

3. Nitration of benzene:
C$_{6}$H$_{6}$ + HNO$_{3}$ (conc.) $\xrightarrow{\text{H}_{2}\text{SO}_{4} \text{ (conc.)}}$ C$_{6}$H$_{5}$NO$_{2}$ (nitrobenzene). Thus, [C] is nitrobenzene.

4. Chlorination of nitrobenzene:
Nitrobenzene is a meta-directing group due to the strong electron-withdrawing effect of the -NO$_{2}$ group. Therefore, electrophilic substitution (chlorination) occurs at the meta position.
C$_{6}$H$_{5}$NO$_{2}$ + Cl$_{2}$ $\xrightarrow{\text{Anhydrous AlCl}_{3}}$ m-chloronitrobenzene. Thus, [D] is m-chloronitrobenzene.

Comparing these results with the provided options, the sequence corresponds to the fourth set of images.

Answer: Figure

Hence, the correct answer is option: 'D'.

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