A chemical reaction produces a mixture of two isomers. These isomers have a small difference in their boiling points, do not exhibit hydrogen bonding, and are typically separated by fractional distillation. Which of the following reactions yields a product mixture that best matches these characteristics?

Step-by-step solution

Nitration of toluene yields a mixture of o -nitrotoluene and p -nitrotoluene. These isomers do not exhibit hydrogen bonding and have a small difference in their boiling points, making fractional distillation the suitable separation method. Nitration of phenol yields o -nitrophenol and p -nitrophenol, which exhibit intramolecular and intermolecular hydrogen bonding respectively, and are separated by steam distillation. Chlorination of chlorobenzene yields o -dichlorobenzene and p -dichlorobenzene, which are separate