Question #cfa2f

1 Answer
Feb 18, 2017

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Structural formulae of 5 possible constitutional isomers of the alkane of molecular formula C_6H_14C6H14 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_6H_13ClC6H13Cl,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"3methylpentane

In this alkane

Replacement of one H-atom linked with C_1 and C_5C1andC5 by Cl atom will give same monochloro isomer.

Replacement of one H-atom linked with C_2and C_4C2andC4 by Cl atom will give same monochloro isomer.

Replacement of one H-atom linked with C_3and C_6C3andC6 by Cl atom will give two different monochloro isomers.