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NEET 2026
Exam
NEET
Year
2026
Subject
Chemistry
Chapter
Chapter

NEET 2026 · Chemistry · Chapter

Identify the intermediate compound 'P' in the given chemical...

Identify the intermediate compound 'P' in the given chemical reaction sequence:
Identify the intermediate compound 'P' in the given chemical reaction sequence:

Options

  1. AC6H5CH2Cl\text{C}_6\text{H}_5\text{CH}_2\text{Cl}
  2. BC6H5CHCl2\text{C}_6\text{H}_5\text{CHCl}_2
  3. CC6H5CCl3\text{C}_6\text{H}_5\text{CCl}_3
  4. Do-Cl-C6H4CH3o\text{-Cl-C}_6\text{H}_4\text{CH}_3

Correct answer

B. C6H5CHCl2\text{C}_6\text{H}_5\text{CHCl}_2

Step-by-step solution

The reaction of toluene with Cl2\text{Cl}_2 in the presence of sunlight (hνh\nu) proceeds via a free radical substitution mechanism at the side chain (benzylic position).

Since the final product upon hydrolysis is benzaldehyde (C6H5CHO\text{C}_6\text{H}_5\text{CHO}), the intermediate compound P must be a geminal dihalide. Hydrolysis of a gem-dihalide yields an unstable gem-diol, which readily loses a water molecule to form an aldehyde.

Therefore, toluene reacts with two equivalents of Cl2\text{Cl}_2 to form benzal chloride (C6H5CHCl2\text{C}_6\text{H}_5\text{CHCl}_2) as the intermediate P.

The reaction sequence is:
C6H5CH3→2Cl2,hνC6H5CHCl2 (P)\text{C}_6\text{H}_5\text{CH}_3 \xrightarrow{2\text{Cl}_2, h\nu} \text{C}_6\text{H}_5\text{CHCl}_2 \text{ (P)}

C6H5CHCl2→H2O,373 K[C6H5CH(OH)2]→−H2OC6H5CHO\text{C}_6\text{H}_5\text{CHCl}_2 \xrightarrow{\text{H}_2\text{O}, 373\text{ K}} [\text{C}_6\text{H}_5\text{CH(OH)}_2] \xrightarrow{-\text{H}_2\text{O}} \text{C}_6\text{H}_5\text{CHO}

Hence, the intermediate compound P is C6H5CHCl2\text{C}_6\text{H}_5\text{CHCl}_2.

Answer: C6H5CHCl2\text{C}_6\text{H}_5\text{CHCl}_2
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