Question

Draw resonance contributors for the carbanion that would be formed if meta-chloronitrobenzene were to react with hydroxide ion. Why doesn’t the reaction occur?

Short answer

The meta-chloronitrobenzene does not react with hydroxide ions, as the negative charge generated on the benzene ring cannot be delocalized into the nitro substituent.

Step-by-step solution

Resonance contributors 

Resonance contributors constitute the imaginary motion of pi-bonded electrons or lone pair of electrons near the pi bonds. All the resonance contributors of a molecule or an ion comprises of the same charge.

Reason for meta-chloronitrobenzene not reacting with the hydroxide ion

From the resonance contributors, it is observed that the meta-chloronitrobenzene does not react with hydroxide ions as the negative charge generated on the benzene ring cannot be delocalized into the nitro substituent. The reaction is as shown below.

Resonance contributors of meta-chloronitrobenzene

The electron delocalization onto the nitro substituent happens if the nitro substituent is ortho or para to the site of the nucleophilic attack.