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Haloalkanes and Haloarenes
Free Radical Halogenation and Stereochemistry
1 question from 1 paper, each with its answer.
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Concepts tested
- Racemic product through planar radical
All Questions
2001 AIPMT 1 question
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$CH_3-CH_2-CH(Cl)-CH_3$ obtained by chlorination of n-butane, will be : -Chlorination of n-butane at C-2 goes by a free radical mechanism: $CH_3CH_2CH_2CH_3 \rightarrow CH_3CH_2\dot{C}HCH_3 \rightarrow CH_3CH_2CHClCH_3$
The intermediate secondary free radical is $sp^2$ hybridised and planar.
The chlorine molecule can attack this planar radical equally from both faces, giving the two enantiomers of 2-chlorobutane in equal amounts.
So the product is a racemic mixture (optically inactive). It cannot be a meso form, since 2-chlorobutane has only one chiral centre.