Which of the following has the shortest C-Cl | vedclass

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(D) The bond length of the $C-Cl$ bond depends on the extent of resonance. In $Cl-CH=CH-NO_2$,the $-NO_2$ group is a strong electron-withdrawing group

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$Cl-CH=CH-NO_2$

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(D) The bond length of the $C-Cl$ bond depends on the extent of resonance. In $Cl-CH=CH-NO_2$,the $-NO_2$ group is a strong electron-withdrawing group ($-M$ effect),while the $Cl$ atom acts as an electron donor ($+M$ effect). This creates a strong conjugation effect where the lone pair on $Cl$ is delocalized towards the $NO_2$ group,increasing the double bond character of the $C-Cl$ bond. Greater double bond character leads to a shorter bond length. Therefore,$Cl-CH=CH-NO_2$ has the shortest $C-Cl$ bond.

Column-$I$	Column-$II$
$(i)$ $R-Cl + NaI \xrightarrow{\text{dry acetone}} R-I + NaCl$	$(a)$ Swarts reaction
$(ii)$ $CH_3-Br + AgF \xrightarrow{\Delta} CH_3-F + AgBr$	$(b)$ Wurtz reaction
$(iii)$ $R-X + Mg$ $\xrightarrow{\text{dry ether}} R-Mg-X$ $\xrightarrow{H_2O} RH + Mg(OH)X$	$(c)$ Finkelstein reaction
	$(d)$ Grignard reaction

Which of the following has the shortest $C-Cl$ bond?

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