Singlet methylene :CH2 inserts into the C-H bonds of 2-methylbutane, (CH3)2CH-CH2-CH3. How many different constitutional isomers of C6H14 can be formed? (Count structural isomers only. All the products are achiral, so there is no stereoisomer ambiguity.)

JEE Main levelNumerical answerDifficulty 2 of 3g3097

Singlet methylene $: CH X_{2}$ inserts into the C-H bonds of 2-methylbutane, $(CH X_{3}) X_{2} CH - CH X_{2} - CH X_{3}$ . How many different constitutional isomers of $C X_{6} H X_{14}$ can be formed? (Count structural isomers only. All the products are achiral, so there is no stereoisomer ambiguity.)

Numerical answer type, tolerance 0.5.

Insertion into a C-H bond converts that carbon's H into a

CH X_{3}

branch or extends the chain. The distinct H sets are: the two equivalent

CH X_{3}

on C-2 giving 3-methylpentane, the C-2 methine giving 2,2-dimethylbutane, the C-3 methylene giving 2,3-dimethylbutane, and the terminal

CH X_{3}

of the ethyl group giving 2-methylpentane. Total 4.