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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3146

Which of the following C-H bonds has the lowest bond dissociation energy?

  1. Aa ring C-H bond of benzene
  2. Bthe tertiary C-H of 2-methylpropane
  3. Cthe C-H bond of methane
  4. Dthe CH hydrogens of diphenylmethane,

Answer: D

The bond that gives the most stabilised radical on cleavage is the weakest. Diphenylmethane gives the diphenylmethyl radical, delocalised over two rings (BDE about 84 kcal/mol). 2-Methylpropane gives a tertiary radical (about 96), methane gives a methyl radical (about 105), and benzene gives a phenyl radical with the electron in a orbital (about 112).
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