Which of the following isomeric heptanes can yield seven different monochlorinated products upon free radical chlorination?

2,2-Dimethylpentane

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2-Methylhexane

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3-Methylhexane

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2,4-Dimethylpentane

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Solution

The correct option is C 3-Methylhexane
In 3-methylhexane, none out of the seven carbon atoms are equivalent and it gives seven different monochlorinated products upon free radical chlorination.

$C H_{2} C l - C H_{2} - C H_{3} | C H - C H_{2} - C H_{2} - C H_{3}$

$C H_{3} - C H C l - C H_{3} | C H - C H_{2} - C H_{2} - C H_{3}$

$C H_{3} - C H_{2} - C H_{3} | C C l - C H_{2} - C H_{2} - C H_{3}$

$C H_{3} - C H_{2} - C H_{2} C l | C H - C H_{2} - C H_{2} - C H_{3}$

$C H_{3} - C H_{2} - C H_{3} | C H - C H C l - C H_{2} - C H_{3}$

$C H_{3} - C H_{2} - C H_{3} | C H - C H_{2} - C H C l - C H_{3}$

$C H_{3} - C H_{2} - C H_{3} | C H - C H_{2} - C H_{2} - C H_{2} C l$

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