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Question

Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R).
Assertion (A) : Carbon halogen bond in aryl and vinyl halides are unusually shorter.
Reason (R) : Chlorobenzene, and vinyl chlorides undergo $S_N1$ and $S_N2$ reaction in general.
In the light of the above statements, choose the most appropriate answer from the options given below :

The correct answer is
(A) is correct but (R) is not correct

Analysis of Statements:

  • Assertion (A): The statement claims that the carbon-halogen bond in aryl and vinyl halides is unusually shorter.
    • In aryl halides (like chlorobenzene), the C-X bond has partial double bond character due to resonance between the benzene ring and the halogen's lone pairs. This resonance effect shortens the bond compared to a single bond.
    • In vinyl halides (like vinyl chloride), the carbon atom attached to the halogen is sp2 hybridized. sp2 hybridized orbitals have more 's' character than sp3 hybridized orbitals (found in alkyl halides). This increased 's' character leads to a shorter and stronger C-X bond.
    • Therefore, Assertion (A) is correct.
  • Reason (R): The statement claims that chlorobenzene and vinyl chlorides undergo $S_N1$ and $S_2$ reactions in general.
    • Aryl halides (like chlorobenzene) are generally unreactive towards nucleophilic substitution reactions ($S_N1$ and $S_N2$). This is because the C-X bond is strong due to partial double bond character, and the formation of an aryl carbocation (needed for $S_N1$) is highly unfavorable.
    • Vinyl halides are also resistant to nucleophilic substitution. $S_N2$ reactions are hindered sterically, and $S_N1$ reactions are difficult due to the instability of the vinyl carbocation.
    • Therefore, Reason (R) is incorrect.

Conclusion:

Based on the analysis, Assertion (A) is correct, while Reason (R) is incorrect.

The most appropriate answer is that (A) is correct but (R) is not correct.

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