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Basics of Organic Chemistry question

2006 · Shift 0 · Q8
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Basics of Organic Chemistry question

2006 · Shift 0 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The increasing order of stability of the following free radicals is
  1. A
    (C6H5)2C∙H{({C_6}{H_5})_2}\mathop C\limits^ \bullet H(C6​H5​)2​C∙​H<(C6H5)3C∙{({C_6}{H_5})_3}\mathop C\limits^ \bullet(C6​H5​)3​C∙​<(CH3)3C∙{(C{H_3})_3}\mathop C\limits^ \bullet(CH3​)3​C∙​<(CH3)2C∙H{(C{H_3})_2}\mathop C\limits^ \bullet H(CH3​)2​C∙​H
  2. B
    (CH3)2C∙H{(C{H_3})_2}\mathop C\limits^ \bullet H(CH3​)2​C∙​H<(CH3)3C∙{(C{H_3})_3}\mathop C\limits^ \bullet(CH3​)3​C∙​<(C6H5)2C∙H{({C_6}{H_5})_2}\mathop C\limits^ \bullet H(C6​H5​)2​C∙​H<(C6H5)3C∙{({C_6}{H_5})_3}\mathop C\limits^ \bullet(C6​H5​)3​C∙​
  3. C
    (CH3)2C∙H{(C{H_3})_2}\mathop C\limits^ \bullet H(CH3​)2​C∙​H<(CH3)3C∙{(C{H_3})_3}\mathop C\limits^ \bullet(CH3​)3​C∙​<(C6H5)3C∙{({C_6}{H_5})_3}\mathop C\limits^ \bullet(C6​H5​)3​C∙​<(C6H5)2C∙H{({C_6}{H_5})_2}\mathop C\limits^ \bullet H(C6​H5​)2​C∙​H
  4. D
    (C6H5)3C∙{({C_6}{H_5})_3}\mathop C\limits^ \bullet(C6​H5​)3​C∙​<(C6H5)2C∙H{({C_6}{H_5})_2}\mathop C\limits^ \bullet H(C6​H5​)2​C∙​H<(CH3)3C∙{(C{H_3})_3}\mathop C\limits^ \bullet(CH3​)3​C∙​<(CH3)2C∙H{(C{H_3})_2}\mathop C\limits^ \bullet H(CH3​)2​C∙​H
View written solutionFree

Correct answer: B

  1. Identify the radicals

The given radicals are:

  • (CH3)2C˙H{(CH_3)_2\dot{C}H}(CH3​)2​C˙H : secondary alkyl radical
  • (CH3)3C˙{(CH_3)_3\dot{C}}(CH3​)3​C˙ : tertiary alkyl radical
  • ((C6H5)2C˙H){((C_6H_5)_2\dot{C}H)}((C6​H5​)2​C˙H) : diphenylmethyl radical
  • ((C6H5)3C˙){((C_6H_5)_3\dot{C})}((C6​H5​)3​C˙) : triphenylmethyl radical
  1. Recall the factors affecting free radical stability

Free radicals are stabilized mainly by:

  • Hyperconjugation from alkyl groups
  • Resonance delocalization into adjacent π\piπ systems

Now compare:

  • Alkyl radicals are stabilized by hyperconjugation.
  • Benzylic/phenyl-substituted radicals are much more stabilized because the unpaired electron can delocalize by resonance over phenyl rings.
  • More phenyl rings attached to the radical center ⇒\Rightarrow⇒ more resonance stabilization.

Thus,

  • (CH3)3C˙{(CH_3)_3\dot{C}}(CH3​)3​C˙ is more stable than (CH3)2C˙H{(CH_3)_2\dot{C}H}(CH3​)2​C˙H due to greater hyperconjugation.
  • ((C6H5)2C˙H){((C_6H_5)_2\dot{C}H)}((C6​H5​)2​C˙H) is more stable than (CH3)3C˙{(CH_3)_3\dot{C}}(CH3​)3​C˙ because resonance stabilization from two phenyl rings is stronger than alkyl hyperconjugation.
  • ((C6H5)3C˙){((C_6H_5)_3\dot{C})}((C6​H5​)3​C˙) is the most stable because the unpaired electron is delocalized over three phenyl rings.
  1. Write the increasing order

Therefore, the increasing order of stability is:

(CH3)2C˙H<(CH3)3C˙<(C6H5)2C˙H<(C6H5)3C˙(CH_3)_2\dot{C}H < (CH_3)_3\dot{C} < (C_6H_5)_2\dot{C}H < (C_6H_5)_3\dot{C}(CH3​)2​C˙H<(CH3​)3​C˙<(C6​H5​)2​C˙H<(C6​H5​)3​C˙
  1. Match with the options

This corresponds to Option B.

  1. Comparison with stored answer

Stored correct answer = B

Our derived answer = B

So, the answers agree.

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