JEE MainChemistryGeneral Organic Chemistry
An aromatic compound P having the molecular formula C₆H₆O reacts with dilute HNO₃ to yield two isomers A and B . Isomer A is steam volatile due to intramolecular hydrogen bonding, whereas isomer B is not steam volatile. Isomer B is treated with aqueous NaOH followed by the addition of ethyl bromide to yield compound C . The total number of hydrogen atoms present in one molecule of compound C is
Correct answer
9
Step-by-step solution
Compound P ( C₆H₆O ) is phenol. Nitration of phenol with dilute HNO₃ yields a mixture of ortho-nitrophenol and para-nitrophenol. Ortho-nitrophenol (isomer A ) is steam volatile due to intramolecular hydrogen bonding, while para-nitrophenol (isomer B ) is not steam volatile due to intermolecular hydrogen bonding. When para-nitrophenol ( B ) is treated with aqueous NaOH , it forms sodium para-nitrophenoxide. This phenoxide ion undergoes Williamson ether synthesis upon reaction with ethyl bromide ( CH₃CH₂Br ) to yield