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Question

How many monochloro structural isomers are expected in free radical monochlorination of 2methylbutane?

A
2
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B
3
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C
4
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D
5
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E
6
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Solution

The correct option is E 6
Number of mono chloro isomers depends upon the types of hydrogen atoms present in the substate alkane. The structure of 2methylbutane is
dCH3cCH2bHC|CaH3aCH3
Because of the presence of four types of hydrogen, it gives four+two(d and l forms) = six monochloro products on monochlorination as
CH3CH2C|HCH3CH3Cl2hvCH3CH2˙CHCH2Cld and l forms1-chloro-2-methyl butane+CH3CH2Cl|C|CH3CH32chloro2methylbutane

+CH3˙C|ClHCH(CH3)22chloro3methylbutane+CH2ClCH2C|HCH3CH31chloro3methylbutane

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