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Question 63

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The products formed in the following reaction sequence are :

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We need to determine the final products formed in the given reaction sequence starting from nitrobenzene.

Reaction Sequence Step-by-Step:

  • Step 1: Bromination ($$\text{Br}_2 / \text{AcOH}$$)
    Nitrobenzene undergoes electrophilic aromatic substitution. Since the nitro group ($$-\text{NO}_2$$) is strongly deactivating and meta-directing, bromination occurs at the meta-position to form 1-bromo-3-nitrobenzene.
  • Step 2: Reduction ($$\text{Sn} / \text{HCl}$$)
    The nitro group ($$-\text{NO}_2$$) is selectively reduced to a primary amino group ($$-\text{NH}_2$$), yielding 3-bromoaniline.
  • Step 3: Diazotization ($$\text{NaNO}_2 + \text{HCl}$$)
    The amino group reacts with nitrous acid at low temperature to form a diazonium salt intermediate: 3-bromobenzenediazonium chloride.
  • Step 4: Reductive Deamination ($$\text{EtOH}$$)
    Treating the diazonium salt with ethanol ($$\text{CH}_3\text{CH}_2\text{OH}$$) reduces the diazonium group ($$-\text{N}_2^+\text{Cl}^-$$) to a hydrogen atom ($$-\text{H}$$), releasing nitrogen gas ($$\text{N}_2$$). Concurrently, ethanol is oxidized to acetaldehyde ($$\text{CH}_3\text{CHO}$$).

Conclusion:

The final organic products formed at the end of the sequence are bromobenzene and acetaldehyde ($$\text{CH}_3\text{CH}=\text{O}$$).

Answer: Option C

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