Question

5. When ortho-bromonitrobenzene is treated with NaOH at elevated temperature, only one product is formed. (a) Draw the product. (b) Identify the intermediate formed en route to the product. (c) Would the reaction occur if the starting compound were meta-bromonitrobenzene

Answer 1

The product formed is orthonitrophenol

Step-by-step explanation:

The compound orthonitrophenol is formed when ortho-bromonitrobenzene is treated with NaOH at elevated temperature.

The reaction leads to the formation of an intermediate stabilized by resonance. This intermediate can not be formed by the meta isomer because a resonance stabilized intermediate can not be formed and the product is not stabilized by intramolecular hydrogen bonding hence this reaction will not occur.