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Question

The maximum number of isomers (including stereoisorners) that are possible on monochlorination otthe following compound, is :
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A
8
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B
6
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C
3
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D
9
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Solution

The correct option is A 8
Isomers of 3-methylpentane are four and stereoisomers are eight.
1-Chloro-3-methyl pentane-43%
2-Chloro-3-methyl pentane-29%(2 stereocenters and chiral molecule)
3-Chloro-3-methyl pentane-7.1%
1-Chloro-2-ethyl butane-21%.
Two stereoisomers give four enantiomers or two pairs. Each of the molecule in either pair of enantiomers is a diastereomer of either molecule in other pair. So in total 8 isomers are possible.

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