The compound shown is nitrated with dilute nitric acid at 298 K. The mixture is then steam distilled. Which structure is the steam-volatile product?

The compound is phenol; dilute nitric acid gives a mixture of 2-nitrophenol and 4-nitrophenol. The 2-isomer has an intramolecular hydrogen bond, so it does not associate with other molecules and is steam volatile. The 4-isomer forms intermolecular hydrogen bonds and remains in the flask. The meta isomer is not formed, and picric acid needs forcing conditions.