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Arrange the following free radicals in order of increasing stability:

1. (CH3)2CH < (CH3)3C < (C6H5)2CH < (C6H5)3C
2. (C6H5)2CH < (C6H5)3C < (CH3)3C < (CH3)2CH
3. (CH3)3C < (CH3)2CH < (C6H5)2CH < (C6H5)3C
4. (C6H5)3C < (C6H5)2CH < (CH3)3C < (CH3)2CH

Correct answer: (CH3)2CH < (CH3)3C < (C6H5)2CH < (C6H5)3C

Solution

Radical stability increases with hyperconjugation/resonance: (CH3)2CH (2-degree alkyl) < (CH3)3C (3-degree alkyl) < (C6H5)2CH (benzylic, 2 rings) < (C6H5)3C (triphenylmethyl, 3 rings, most resonance-stabilized). Correct order: (CH3)2CH < (CH3)3C < (C6H5)2CH < (C6H5)3C.

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