Among the following compounds, which one has the shortest C - Cl bond?
Show Hint
- \(\mathrm{H_3C-Cl}\)
The Correct Option is D
Solution and Explanation
An sp2 carbon has more s-character (33%) than sp3 (25%), so its bond to Cl is shorter.
In vinyl chloride the lone pair on Cl is delocalised into the C=C (\(\mathrm{CH_2=CH-\ddot{Cl} \leftrightarrow {}^-CH_2-CH=Cl^+}\)), giving the C-Cl bond partial double-bond character.
Hence the shortest C-Cl bond is in vinyl chloride (about 1.72 A against about 1.78 A in alkyl chlorides).
Answer: (4) \(\mathrm{CH_2=CH-Cl}\)
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