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Haloalkanes and Haloarenes question

2020 · 4 Sep · Shift 2 · Q5
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  5. /2020 · 4 Sep · Shift 2 · Q5

Haloalkanes and Haloarenes question

2020 · 4 Sep · Shift 2 · Q5

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Among the following compounds, which one has the shortest C – Cl bond?
  1. A
    H3CH_3CH3​C - ClClCl
  2. B
    JEE Main 2020 (Online) 4th September Evening Slot Chemistry - Haloalkanes and Haloarenes Question 111 English Option 2
  3. C
    JEE Main 2020 (Online) 4th September Evening Slot Chemistry - Haloalkanes and Haloarenes Question 111 English Option 3
  4. D
    JEE Main 2020 (Online) 4th September Evening Slot Chemistry - Haloalkanes and Haloarenes Question 111 English Option 4
View written solutionFree

Correct answer: D

  1. Key idea: The length of a C–Cl bond depends mainly on the hybridisation of the carbon atom attached to chlorine.

  2. General trend of bond length:

    • For a carbon with more sss-character, the bond becomes shorter.
    • Hybridisation and sss-character:
      • sp3sp^3sp3 carbon: 25%25\%25% sss-character
      • sp2sp^2sp2 carbon: 33%33\%33% sss-character
      • spspsp carbon: 50%50\%50% sss-character Hence, C–Cl bond length: sp<sp2<sp3\text{C–Cl bond length: } sp < sp^2 < sp^3C–Cl bond length: sp<sp2<sp3
  3. Evaluate the given visible option:

    • A: CH3ClCH_3ClCH3​Cl Here carbon is sp3sp^3sp3 hybridised, so the C–Cl bond is relatively longer.
  4. Most likely correct principle among typical options: In standard JEE-type questions on this topic, the compound with the shortest C–Cl bond is the one where chlorine is attached to an spspsp-hybridised carbon, such as chloroethyne (HC≡CClHC\equiv CClHC≡CCl), because of maximum sss-character.

  5. Conclusion: Since the stored correct answer is D, option D must correspond to the compound having chlorine attached to the carbon with maximum sss-character, giving the shortest C–Cl bond.

Therefore, the shortest C–Cl bond is in option D.

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