Exams › JEE Main › Chemistry

Which of the following compounds has the shortest carbon-chlorine (C-Cl) bond?

1. H3C-Cl
2. (CH3)3C-Cl
3. CH2=CH-Cl
4. 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.

Related JEE Main Chemistry questions

• Why is the chlorine atom in vinyl chloride comparatively less reactive?
• What is the product obtained when neopentyl bromide undergoes the Wurtz reaction?
• Which of the following reactions is most likely to produce a hydrocarbon in high yield with ease?
• Which of the following reactions proceeds by an S_N2 mechanism?
• Identify the incorrect statement among the following:
• When chloroform is exposed to air and sunlight by keeping it open, what product is formed?

⚔️ Practice JEE Main Chemistry free + battle 1v1 →