JEE Main · 2023 · Shift-IhardHC-104

The major product P formed in the given reaction is:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

The major product P formed in the given reaction is: image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerd

image

Detailed Solution

Step 1: Identify the Starting Material

From the image: a naphthalene ring with \ceCH2CH3\ce{-CH2CH3} (ethyl), \ceCH=CH2\ce{-CH=CH2} (vinyl), and \ceCOOCH3\ce{-COOCH3} (methyl ester) substituents.

Step 2: Hot Alkaline KMnO4 Oxidation

Hot alkaline \ceKMnO4\ce{KMnO4} oxidizes:

  • Alkyl side chains on benzene ring to \ceCOOH\ce{-COOH}
  • Vinyl group \ceCH=CH2\ce{-CH=CH2} to \ceCOOH\ce{-COOH} (oxidative cleavage)
  • Methyl ester \ceCOOCH3\ce{-COOCH3} hydrolyzes to \ceCOOH\ce{-COOH} under alk. conditions
  • The naphthalene ring itself may be cleaved to give multiple \ceCOOH\ce{-COOH} groups

Step 3: Product P image All oxidizable side chains \rightarrow \ceCOOH\ce{-COOH}. The complex oxidation gives a phthalic acid or naphthalenedicarboxylic acid type product (option d from the image).

Key Points:

  • Hot alk. \ceKMnO4\ce{KMnO4}: oxidizes all alkyl side chains to \ceCOOH\ce{-COOH}
  • \ceCH=CH2\ce{-CH=CH2} oxidatively cleaved to \ceCOOH\ce{-COOH}
  • Ester groups hydrolyze under alkaline conditions
  • Naphthalene ring also susceptible to oxidation under harsh conditions

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The major product P formed in the given reaction is: (JEE Main 2023) | Canvas Classes