Which of the following has the shortest C - C l bond?

1. $\mathrm{C}\mathrm{l}-\mathrm{C}\mathrm{H}=\mathrm{C}{\mathrm{H}}_2$
2. $\mathrm{C}\mathrm{l}-\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}-\mathrm{N}{\mathrm{O}}_2$
3. $\mathrm{C}\mathrm{l}-\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}-\mathrm{C}{\mathrm{H}}_3$
4. $\mathrm{C}\mathrm{l}-\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}-\mathrm{O}\mathrm{C}{\mathrm{H}}_3$

Solution

  Due to –M effect of $-{\text{NO}}_{\text{2}}$ and + M effect of Cl more D.B. character between C – Cl bond. So shortest bond length.

Asked in: JEE Main 2020 (09 Jan Shift 2)

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