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Question 41

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'X' is:

1. Formation of the Carbocation (Protonation)

The reaction uses hydrofluoric acid ($$\text{HF}$$) as an acid catalyst. The exocyclic double bond of methylenecyclohexane undergoes protonation according to Markovnikov's rule:

  • The $$H^+$$ from $$\text{HF}$$ adds to the terminal carbon ($$=\text{CH}_2$$), converting it into a methyl group ($$-\text{CH}_3$$).
  • This creates a highly stable tertiary ($$3^\circ$$) carbocation at the ring carbon (the 1-methylcyclohexyl cation).

2. Electrophilic Aromatic Substitution (Friedel-Crafts Alkylation)

Benzene acts as the nucleophile and attacks this stable tertiary carbocation:

  • The $$\pi$$-electrons of the benzene ring attack the positively charged carbon atom of the 1-methylcyclohexyl cation.
  • Subsequent deprotonation restores the aromaticity of the benzene ring.
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