JEE Main · 2020 · Shift-IIhardHALO-104

In the following reaction sequence, structure of A and B respectively will be:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

In the following reaction sequence, structure of A and B respectively will be: image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerc

image

Detailed Solution

Step 1: Analyze the starting material

Cyclic ketone with \ceCH2Br\ce{-CH2Br} side chain

Step 2: Reaction with HBr

HBr can:

  • Protonate the ketone oxygen
  • Add to any C=C if present
  • React with \ceCH2Br\ce{-CH2Br} (unlikely - already has Br)

If there's a ketone, HBr might not react directly. The structure needs clarification from the image.

Step 3: Reaction with Na/Ether (Wurtz coupling)

Wurtz reaction: \ce2RBr+2Na>[Ether]RR+2NaBr\ce{2 R-Br + 2 Na ->[Ether] R-R + 2 NaBr}

This couples two alkyl bromides.

Intermolecular product B means two molecules couple together.

Step 4: Determine structures

Given answer (c):

  • A: Product after HBr treatment (likely adds Br somewhere)
  • B: Coupled product (two A molecules joined)

The reaction sequence suggests:

  1. HBr adds to create more Br sites
  2. Na/Ether couples the molecules

Answer: (c)

Key Reactions:

Wurtz reaction:

  • Couples alkyl halides
  • Uses Na metal in dry ether
  • Forms C-C bond
  • Intermolecular: \ce2RX>RR\ce{2 R-X -> R-R}

Wurtz-Fittig:

  • Couples aryl and alkyl halides
  • \ceArX+RX+2Na>ArR\ce{Ar-X + R-X + 2Na -> Ar-R}

Limitations:

  • Works best with primary halides
  • Secondary/tertiary give elimination
  • Can give mixture of products

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In the following reaction sequence, structure of A and B respectively will be: (JEE Main 2020) | Canvas Classes