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CH3OCH=CHNO2 I
CH2=CHNO2II
CH2=CHClIII
CH2=CH2IV

Which of the following is the correct order of C=C bond lengths among these compounds?

A
I>II>III>IV
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B
IV>III>II>I
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C
I>III>II>IV
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D
II>III>I>IV
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Solution

The correct option is D I>II>III>IV
Ethylene contains carbon-carbon double bond.
In vinyl chloride, the lone pair of chlorine is in resonance with carbon-carbon double bonds. This reduces the bond order of the carbon-carbon double bond.
In vinyl nitrite, the strong electron-withdrawing nitro group reduces the electron density of carbon-carbon double bond and further reduces the bond order of carbon-carbon double bond.
In compound (I) due to the resonance of lone pair of oxygen with carbon-carbon double bond and the electron-withdrawing effect of the nitro group, the bond order is further reduced.
Hence, the correct order of carbon-carbon bond lengths is I>II>III>IV.

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