JEE PYQ: General Organic Chemistry Question 20
Question 20 - 2020 (04 Sep Shift 2)
Among the following compounds, which one has the shortest C–Cl bond?
(1) $(\text{CH}_3)_3\text{C}-\text{Cl}$ (neopentyl chloride)
(2) $\text{HC}(=\text{CH}_2)-\text{Cl}$ (vinyl type chloride)
(3) $\text{H}_3\text{C}-\text{Cl}$ (methyl chloride)
(4) $\text{CH}(=\text{CH}_2)-\text{Cl}$ (allyl/vinyl chloride)
Show Answer
Answer: (4)
Solution
Due to conjugation of lone pair of Cl with $\pi$ bond, partial double bond character decreases bond length. That’s why compound (4) has shortest C-Cl bond length.
BETA
