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Haloalkanes and Haloarenes question

2023 · 15 Apr · Shift 1 · Q3
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Haloalkanes and Haloarenes question

2023 · 15 Apr · Shift 1 · Q3

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
The major product formed in the Friedel-Craft acylation of chlorobenzene is
  1. A
    JEE Main 2023 (Online) 15th April Morning Shift Chemistry - Haloalkanes and Haloarenes Question 54 English Option 1
  2. B
    JEE Main 2023 (Online) 15th April Morning Shift Chemistry - Haloalkanes and Haloarenes Question 54 English Option 2
  3. C
    JEE Main 2023 (Online) 15th April Morning Shift Chemistry - Haloalkanes and Haloarenes Question 54 English Option 3
  4. D
    JEE Main 2023 (Online) 15th April Morning Shift Chemistry - Haloalkanes and Haloarenes Question 54 English Option 4
View written solutionFree

Correct answer: A

  1. Reaction involved

    Friedel–Crafts acylation of chlorobenzene means introducing an acyl group, −COR-COR−COR, onto the benzene ring in presence of a Lewis acid such as AlCl3\text{AlCl}_3AlCl3​.

  2. Directive effect of chlorine

    In chlorobenzene, chlorine shows:

    • −I-I−I effect: deactivates the ring
    • +M+M+M effect: donates lone pair electron density to the ring by resonance

    Because of resonance donation, chlorine is an ortho/para-directing group.

  3. Relative formation of ortho and para products

    Although both ortho and para acylated products are formed, the para product is major because:

    • the acyl group is bulky,
    • steric hindrance is less at the para position than at the ortho position.
  4. Conclusion

    Therefore, the major product in Friedel–Crafts acylation of chlorobenzene is the para-acyl derivative of chlorobenzene.

    So the correct option must be the structure corresponding to: p-chloro aryl ketonep\text{-chloro aryl ketone}p-chloro aryl ketone i.e. acyl group enters at the para position with respect to chlorine.

  5. Comparison with stored answer

    The stored correct answer is A. Since the actual structures of options A–D are not visible, I cannot verify directly from the figures. However, if option A represents the para-acylated chlorobenzene, then the stored answer is correct.

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