Radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH3)4C, is a good way to prepare neopentyl chloride, (CH3)3CCH2Cl. Why?

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Aviriloreapa Aviriloreapa

19-05-2017
Chemistry

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Radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH3)4C, is a good way to prepare neopentyl chloride, (CH3)3CCH2Cl. Why?

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JavierCollante JavierCollante · Answer 1 · 2017-05-19T03:07:29+02:00

radical chlorination is not as selective as radical bromination. the rate in which it reacts with primary, secondary or tertiary hydrogens is not that great of a difference.

So, in pentane, CH3CH2CH2CH2CH3, by the reaction with Cl2, the chlorine group can attach to any of the carbons which would form many isomers and not specifically 1-=chloropentane. In neopentane, (CH3)4C, it is different. each of the H atoms is equivalent. So no matter which one be substituted, only one product, (CH3)CCH2Cl, can be prepared.