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Question

The monochloro isomer that predominates in the mixture resulting from the free-radical chlorination of CH3CH2CH2CH=CH2 is:

A
ClCH2CH2CH2CH2CH=CH2
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B
CH3CHClCH2CH=CH2
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C
CH3CH2CHClCH=CH2
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D
CH3CH2CH2CCl=CH2
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Solution

The correct option is C CH3CH2CHClCH=CH2
Given compound is CH3CH2CH2CH=CH2
Primary hydrogens =3
Secondary hydrogens =6
Tertiary hydrogens =1
Mono chloro derivatives relative rates would be
For primary monochloro derivative, the relative rate is 3×1=3
For secondary monochloro derivative, the relative rate is 6×4=24
For tertiary monochloro derivative, the relative rate is 1×5=5
We take selectivity to be 1 for primary, 4 for secondary and 5 for tertiary.
Monochloro isomer that predominates in the mixture resulting from the free-radical chlorination of 1-pentene will be CH3CH2CHClCH=CH2

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