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Question 52

The major product of the following reaction is: 

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  1. The reaction begins with the generation of an initial carbocation intermediate (typically via the protonation and loss of a leaving group like a hydroxyl group or via electrophilic addition to an alkene). The carbocation forms.


  2. Nucleophilic Attack by Chloride Ion ($$\text{Cl}^\ominus$$):

    The chloride ion ($$\text{Cl}^\ominus$$) acts as a nucleophile. It attacks the electron-deficient sp2 hybridized carbocation carbon:

    $$\text{R}^\oplus + \text{Cl}^\ominus \rightarrow \text{R--Cl}$$

Analyzing the Final Product Structure:

Based on the provided mechanism diagram:

  • The parent framework consists of a fused bicyclic ring system (a 6-membered ring fused to a 5-membered or 6-membered ring).
  • An exocyclic group contains an isopropyl-like unit where the rearrangement takes place.
  • The chloride ion attacks the tertiary carbon center bearing the two methyl ($$\text{--CH}_3$$) groups, resulting in a tertiary alkyl chloride derivative as the final stable major product: $$\text{--C(Cl)(CH}_3)_2$$.

Conclusion:

The major product is formed via a thermodynamic pathway favored by the generation of a stable tertiary carbocation intermediate, followed by direct nucleophilic capture by the chloride ion.

Answer: The option corresponding to the structure containing the chlorine atom attached to the tertiary carbon carrying the two methyl groups on the bicyclic framework (Option D).

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