Question
Write hydrocarbon radicals that can be formed as intermediates during monochlorination of 2-methylpropane. Which of them is more stable? Give reasons.
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Answer
During monochlorination of 2-methylpropane, 2-methylpropane gives two types of radicals:
Radical (II) is less stable because it is $1^{\circ}$ and stabilised by one hyper conjugative structure (as it has only $1 \alpha$-hydrogen).
Radical (I) is more stable because it is $3^{\circ}$ and stabilised by nine hyper conjugative structures (as it has $9 \alpha$-hydrogens).
Hence, Radical (I)is more stable.
Radical (II) is less stable because it is $1^{\circ}$ and stabilised by one hyper conjugative structure (as it has only $1 \alpha$-hydrogen).
Radical (I) is more stable because it is $3^{\circ}$ and stabilised by nine hyper conjugative structures (as it has $9 \alpha$-hydrogens).
Hence, Radical (I)is more stable.
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