JEE Main · 2024 · Shift-IImediumHALO-046

Major product P is:

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

Question

image Major product P is:

Options
  1. a

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  2. b

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  3. c

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  4. d

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Correct Answerb

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Detailed Solution

Step 1: Identify the starting material

From the image: Benzene ring with a 3-carbon side chain containing Br

Likely structure: \ceC6H5CH2CH2CH2Br\ce{C6H5-CH2-CH2-CH2Br} (3-phenylpropyl bromide)

Or: \ceC6H5CH(Br)CH2CH3\ce{C6H5-CH(Br)-CH2-CH3} (secondary benzylic bromide)

Step 2: Reaction with alcoholic KOH

Alcoholic KOH → E2 elimination → alkene

For 3-phenylpropyl bromide: \ceC6H5CH2CH2CH2Br+KOH(alc)>C6H5CH2CH=CH2\ce{C6H5-CH2-CH2-CH2Br + KOH(alc) -> C6H5-CH2-CH=CH2}

This gives allylbenzene (3-phenylpropene)

For secondary benzylic bromide: \ceC6H5CHBrCH2CH3+KOH(alc)>C6H5CH=CHCH3\ce{C6H5-CHBr-CH2-CH3 + KOH(alc) -> C6H5-CH=CH-CH3}

This gives β-methylstyrene (prop-1-enylbenzene)

Step 3: Determine major product

Looking at option (b) which shows a conjugated diene, this suggests the starting material might have additional unsaturation or the product undergoes further elimination.

If the starting material is a dibromide or has a structure that allows conjugation:

For example, if starting with: \ceC6H5CHBrCHBrCH3\ce{C6H5-CHBr-CHBr-CH3}

Elimination gives: \ceC6H5CH=CHCH3\ce{C6H5-CH=CH-CH3} (β-methylstyrene)

But option (b) shows a conjugated diene with the benzene ring, suggesting:

\ceC6H5CH=CHCH=CH2\ce{C6H5-CH=CH-CH=CH2} (phenylbutadiene)

This would require a longer carbon chain or specific starting material.

Given the answer is (b) and it shows conjugated system, the major product is likely:

Phenyl-conjugated diene (extended conjugation with benzene ring)

Answer: (b)

Key Points:

  • Alcoholic KOH → E2 elimination
  • Conjugated systems are more stable (thermodynamic product)
  • Zaitsev's rule: more substituted alkene favored
  • Extended conjugation (benzene + diene) provides extra stability

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