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Consider the following compound (X) H–C≡C–CH2–CH(CH3)–CH3 The most stable and least stable carbon radicals, respectively, produced by homolytic cleavage of corresponding C–H bond are:

1. (I), IV
2. (II), III
3. (III), I
4. (IV), I

Correct answer: (III), I

Solution

The stability of carbon radicals is influenced by the degree of substitution; tertiary radicals are more stable than secondary, which are more stable than primary. In this case, radical (III) is tertiary and thus the most stable, while radical (I) is primary and the least stable.

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