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Question

Which of the following molecule is polar as well as planar?

A
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B
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C
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D
None of these
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Solution

The correct option is C
Cis isomer of 1,3-dichloropropa-1,2-diene is clearly polar. Its analogue (Z)-1,4-dichlorobuta-1,2,3-triene is also polar!

In allenes, the molecule is planar if the number of consecutive carbons having carbon-carbon double bonds is even.
Contrarily, in perfluoro-1,2-propadiene, there are three (odd number) such carbon atoms.
If we look at the central carbon atom, it is sp hybridized and the sigma bonds are 180° apart.

The central carbon's two pi bonds have to be mutually perpendicular to each other.
This clearly mandates that the terminal FCF planes also be mutually perpendicular.

By the extension of the same logic, perfluorobuta-1,2,3-triene is planar!

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