Exams › JEE Advanced › Chemistry
Which of the following compounds has the shortest carbon-chlorine (C-Cl) bond?
- H3C-Cl
- (CH3)3C-Cl
- CH2=CH-Cl
- CH2=CH-CH2-Cl
Correct answer: CH2=CH-Cl
Solution
In vinyl chloride (CH2=CH-Cl) the chlorine is attached to an sp2 carbon (more s-character, shorter bond) and its lone pair delocalizes into the C=C double bond, giving the C-Cl bond partial double-bond character. Both effects shorten the bond. In the other compounds chlorine is on an sp3 carbon with no such conjugation, so their C-Cl bonds are longer.
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