A student was given a sample of an unknown liquid and asked to determine as much as possible about its structure. He was told that the compound contained only carbon, hydrogen, and oxygen, and had only one type of functional group. The student found its boiling point to be 206°C. Using mass spectroscopy, he determined its molecular weight to be 138 g/mol. Finally, he took the infrared spectrum of the compound, which is shown below.
From this spectrum, the student quickly reached a conclusion about the functional group. He then turned his attention to the fingerprint region of the compound, which generally has a complicated pattern of peaks that are determined by the structure of the hydrocarbon portion of a molecule. The student decided that the large peak at 750 cm-1 must indicate that this was a disubstituted aromatic compound.
Assuming that all of the student's deductions were correct, which of the following could be the structure of the unknown compound?
