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Topic: Preparation, properties and reactions· Organic Compounds Containing Halogens

Identify compound X in the following sequence of reactions :Toluene (C_6H_5CH_3) Cl_2/h X [373\ K]H_2O Benzaldehyde (C_6H_5CHO)

Identify compound X in the following sequence of reactions :

Toluene (C\(_6\)H\(_5\)CH\(_3\)) \(\xrightarrow{Cl_2/h\nu}\) X \(\xrightarrow[373\ K]{H_2O}\) Benzaldehyde (C\(_6\)H\(_5\)CHO)

reaction scheme and four structure options (benzene ring with Cl, CH2Cl, CHCl2, CCl3)

1. Chlorobenzene (C\(_6\)H\(_5\)Cl)

2. Benzyl chloride (C\(_6\)H\(_5\)CH\(_2\)Cl)

3. Benzal chloride (C\(_6\)H\(_5\)CHCl\(_2\))

4. Benzotrichloride (C\(_6\)H\(_5\)CCl\(_3\))

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Answer: 3. Benzal chloride (C\(_6\)H\(_5\)CHCl\(_2\))

Free-radical chlorination of the side chain (\(\mathrm{Cl_2/h\nu}\)) replaces methyl hydrogens. To get an aldehyde on hydrolysis, the carbon must carry two chlorine atoms.

  1. Toluene with 2 equivalents of \(\mathrm{Cl_2}\), light: \(\mathrm{C_6H_5CHCl_2}\) (benzal chloride) = X.
  2. Hydrolysis with water at 373 K: \(\mathrm{C_6H_5CH(OH)_2}\), a gem-diol, loses water to give \(\mathrm{C_6H_5CHO}\).

\(\mathrm{C_6H_5CCl_3}\) would give benzoic acid; \(\mathrm{C_6H_5CH_2Cl}\) would give benzyl alcohol; chlorobenzene does not form under light. Answer: option (3).

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
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