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Haloalkanes and Haloarenes question

2017 · Shift 0 · Q5
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Haloalkanes and Haloarenes question

2017 · Shift 0 · Q5

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
The major product obtained in the following reaction is : JEE Main 2017 (Offline) Chemistry - Haloalkanes and Haloarenes Question 152 English
  1. A
    C6H5CHC_6H_5CHC6​H5​CH = CHC6H5CHC_6H_5CHC6​H5​
  2. B
    (+) - C6H5CH(Ot−Bu)CH2C6H5C_6H_5CH(Ot-Bu)CH_2C_6H_5C6​H5​CH(Ot−Bu)CH2​C6​H5​
  3. C
    (-) - C6H5CH(Ot−Bu)CH2C6H5C_6H_5CH(Ot-Bu)CH_2C_6H_5C6​H5​CH(Ot−Bu)CH2​C6​H5​
  4. D
    (±\pm±) - C6H5CH(Ot−Bu)CH2C6H5C_6H_5CH(Ot-Bu)CH_2C_6H_5C6​H5​CH(Ot−Bu)CH2​C6​H5​
View written solutionFree

Correct answer: A

  1. Identify the substrate and reagent behavior

    The reaction involves a benzylic halide of the type C6H5CH(X)CH2C6H5C_6H_5CH(X)CH_2C_6H_5C6​H5​CH(X)CH2​C6​H5​ reacting with tert-butoxide text−BuO−t ext{-}BuO^-text−BuO−.

    Here, text−BuO−t ext{-}BuO^-text−BuO− is:

    • a strong base
    • a bulky nucleophile/base

    Therefore, it strongly favors elimination (E2E2E2) over substitution.

  2. Check possible pathways

    Possible products shown are:

    • Elimination product: C6H5CH=CHC6H5C_6H_5CH=CHC_6H_5C6​H5​CH=CHC6​H5​
    • Substitution products: C6H5CH(Otext−Bu)CH2C6H5C_6H_5CH(Ot ext{-}Bu)CH_2C_6H_5C6​H5​CH(Otext−Bu)CH2​C6​H5​ with chiral possibilities: (+),(−),(±)(+), (-), (\pm)(+),(−),(±)
  3. Why elimination is favored

    In benzylic halides, substitution can occur, but with text−BuO−t ext{-}BuO^-text−BuO− the steric hindrance makes backside attack difficult.

    The substrate has a suitable β\betaβ-hydrogen on the adjacent CH2CH_2CH2​ group, so an E2E2E2 reaction can occur easily: C6H5CH(X)CH2C6H5→text−BuO−C6H5CH=CHC6H5C_6H_5CH(X)CH_2C_6H_5 \xrightarrow[t ext{-}BuO^-]{} C_6H_5CH=CHC_6H_5C6​H5​CH(X)CH2​C6​H5​text−BuO−​C6​H5​CH=CHC6​H5​

  4. Stability of the alkene formed

    The alkene obtained is C6H5CH=CHC6H5C_6H_5CH=CHC_6H_5C6​H5​CH=CHC6​H5​ which is stilbene, a highly stabilized alkene due to conjugation with two phenyl rings.

    This makes elimination especially favorable.

  5. Why substitution products are not major

    If substitution occurred, it would give C6H5CH(Otext−Bu)CH2C6H5C_6H_5CH(Ot ext{-}Bu)CH_2C_6H_5C6​H5​CH(Otext−Bu)CH2​C6​H5​ and depending on mechanism could give enantiomers.

    However, because the reagent is bulky and strongly basic, substitution is minor compared with elimination.

  6. Conclusion

    Therefore, the major product is: C6H5CH=CHC6H5C_6H_5CH=CHC_6H_5C6​H5​CH=CHC6​H5​

    So the correct option is A.


Comparison with stored correct answer

Stored correct answer: A

My derived answer: A

They agree.

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