Which of the following carbocations is expected to be most stable?
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Answer
(3) [figure]
Solution
In each cation the positive charge is delocalised by resonance over the three carbons ortho and para to the sp3 (C–H, Y) carbon.
-NO2 is a strong electron-withdrawing group (−I, −R) ⇒ a positive charge on the carbon carrying -NO2 is strongly destabilised.
(1), (2), (4): -NO2 is ortho/para to the sp3 carbon ⇒ one resonance structure places on the carbon bearing -NO2 ⇒ destabilised.
(3): -NO2 is meta to the sp3 carbon ⇒ never comes on the carbon bearing -NO2 ⇒ least destabilised.
∴ Cation (3) is the most stable.
Answer: (3)