Which of the following has the shortest $\mathrm{C}-\mathrm{Cl}$ bond?

(A) $\mathrm{Cl}-\mathrm{CH}=\mathrm{CH}-\mathrm{NO}_{2}$

(B) $\mathrm{Cl}-\mathrm{CH}=\mathrm{CH}-\mathrm{OCH}_{3}$

(C) $\mathrm{Cl}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{3}$

(D) $\mathrm{Cl}-\mathrm{CH}=\mathrm{CH}_{2}$

JEE Main · 2020 · 09 Jan 2020 · Shift 2 · General Organic Chemistry

Which of the following has the shortest

C - Cl

bond?

(A) $Cl - CH = CH - NO_{2}$ ✓ Correct
(B) $Cl - CH = CH - OCH_{3}$
(C) $Cl - CH = CH - CH_{3}$
(D) $Cl - CH = CH_{2}$

Answer: (A)

Solution

The

C - Cl

bond shortens when the attached group withdraws electron density and raises the double-bond character at that carbon. The nitro group is a strong electron-withdrawing substituent that pulls electron density away by resonance and induction, tightening and shortening the

C - Cl

bond, whereas a methoxy group donates electron density and lengthens it. The shortest

C - Cl

bond is therefore in

Cl - CH = CH - N O_{2}

JEE Main · 2020 · 09 Jan 2020 · Shift 2 · Single correct option

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