The product B formed in the following reaction sequence is: (Major product)
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
The product B formed in the following reaction sequence is:
(Major product)
- a
- b
- c
- d✓
Step 1: Identify starting material
"Benzene-propene" likely means allylbenzene (3-phenylpropene) or propenylbenzene:
Structure: (allylbenzene)
Or: (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 ():
Product A = 1-chloro-1-phenylpropane (secondary chloride)
For β-methylstyrene ():
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 ()
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 ()
- KCN/NaCN (ionic) → nitrile ()
- Benzylic position is reactive due to carbocation stability
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