JEE Main Chemistry question

An electrophile E⁺ attacks nitrobenzene to generate an arenium (σ-complex) intermediate. Of the resonance contributors to the possible σ-complexes, which is of lowest energy?

(A)The contributor from ortho attack with + charge adjacent to –NO₂
(B)The contributor from para attack with + charge adjacent to –NO₂
(C)The contributor from ortho attack with + charge directly on the NO₂-bearing carbon
(D)The contributor from meta attack, which never places + charge on the NO₂-bearing carbonCorrect

Answer: (D)

Solution

–NO₂ is a strong electron-withdrawing group; any resonance contributor placing positive charge directly on (or immediately adjacent to) the NO₂-bearing carbon is severely destabilized. Only

See the full step-by-step solution

Create a free account to read the complete working, and practise questions like this in a timed test.

Create a free account

Question ID VK-139033