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Answer 1 · 2017-02-18T05:27:07

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Structural formulae of 5 possible constitutional isomers of the alkane of molecular formula $C_{6} H_{14}$ $C_6H_14$ have been shown in above figure.

The 6carbon atoms of each structural formula have been numbered.
In numbering process equivalent carbon atoms in a particular structural formula have been given same color.

We are to find out that isomer of the alkane which yields four constitutional isomers with the formula $C_{6} H_{13} C l$ $C_6H_13Cl$ ,when reacted with chlorine. This is possible for that isomer of the alkane which has got four types carbon atoms. Observing the color combination given to C-atoms we see that structure III satisfies the condition.

So the compound is $3 - methylpentane$ $3-"methylpentane"$

In this alkane

Replacement of one H-atom linked with $C_{1} and C_{5}$ $C_1 and C_5$ by Cl atom will give same monochloro isomer.

Replacement of one H-atom linked with $C_{2} and C_{4}$ $C_2and C_4$ by Cl atom will give same monochloro isomer.

Replacement of one H-atom linked with $C_{3} and C_{6}$ $C_3and C_6$ by Cl atom will give two different monochloro isomers.

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