JEE Main · 2025 · Shift-IImediumHALO-027

The product B formed in the following reaction sequence is: (Major product)

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

Question

The product B formed in the following reaction sequence is: (Major product) image

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 Answerd

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Detailed Solution

Step 1: Identify starting material

"Benzene-propene" likely means allylbenzene (3-phenylpropene) or propenylbenzene:

Structure: \ceC6H5CH2CH=CH2\ce{C6H5-CH2-CH=CH2} (allylbenzene)

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

Step 2: Reaction with HCl

Addition of HCl to the double bond follows Markovnikov's rule:

  • H goes to the carbon with more H atoms
  • Cl goes to the more substituted carbon

For allylbenzene (\ceC6H5CH2CH=CH2\ce{C6H5-CH2-CH=CH2}): \ceC6H5CH2CH=CH2+HCl>C6H5CH2CHClCH3\ce{C6H5-CH2-CH=CH2 + HCl -> C6H5-CH2-CHCl-CH3}

Product A = 1-chloro-1-phenylpropane (secondary chloride)

For β-methylstyrene (\ceC6H5CH=CHCH3\ce{C6H5-CH=CH-CH3}): \ceC6H5CH=CHCH3+HCl>C6H5CHClCH2CH3\ce{C6H5-CH=CH-CH3 + HCl -> C6H5-CHCl-CH2-CH3}

Product A = 2-chloro-1-phenylpropane (secondary benzylic chloride)

Step 3: Reaction with AgCN

Product A + AgCN → substitution

AgCN is a covalent silver salt → attacks through nitrogen → forms isocyanide (\ceRNC\ce{R-NC})

\ceC6H5CHClCH2CH3+AgCN>C6H5CH(NC)CH2CH3\ce{C6H5-CHCl-CH2-CH3 + AgCN -> C6H5-CH(NC)-CH2-CH3}

Product B = isocyanide at the benzylic position

The NC group is at the secondary benzylic carbon (where Cl was).

Answer: (d)

Key Points:

  • HCl addition to alkenes: Markovnikov's rule
  • AgCN (covalent) → isocyanide (\ceRNC\ce{R-NC})
  • KCN/NaCN (ionic) → nitrile (\ceRCN\ce{R-CN})
  • Benzylic position is reactive due to carbocation stability

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The product B formed in the following reaction sequence is: (Major product) (JEE Main 2025) | Canvas Classes