JEE MainChemistryGeneral Organic Chemistry
Consider the two isomeric products formed when phenol reacts with dilute nitric acid at 298 K . Which of the following statements regarding the physical properties and separation of these isomers is INCORRECT?
Options
- AThe mixture of these isomers can be efficiently separated by steam distillation.
- Bo -nitrophenol is more soluble in water than p -nitrophenol.
- Co -nitrophenol has a lower boiling point than p -nitrophenol.
- Dp -nitrophenol is less volatile in steam due to intermolecular hydrogen bonding.
Correct answer
B. o -nitrophenol is more soluble in water than p -nitrophenol.
Step-by-step solution
The reaction of phenol with dilute HNO ₃ at 298 K yields o -nitrophenol and p -nitrophenol. o -nitrophenol exhibits intramolecular hydrogen bonding (chelation). This prevents the molecules from associating with each other, resulting in a lower boiling point and making it steam volatile. Furthermore, because its polar groups are involved in internal hydrogen bonding, they are less available to form hydrogen bonds with water, making o -nitrophenol less soluble in water. p -nitrophenol exhibits intermolecular hydrogen