A compound with a molecular formula C₉H₁₂ has the following ¹H NMR spectrum. Which of the following structures is consistent with this spectrum?

Question

Quizplus · Accepted Answer

The ¹H NMR spectrum shows 3 distinct signals: - One singlet at around 2.5 ppm (integration of 1H) - One septet at around 7.5 ppm (integration of 1H) - One broad signal around 8-9 ppm (integration of 1H) Structure I can be eliminated because it does not have any hydrogens attached to sulfur that could give rise to the singlet at 2.5 ppm. Structure II can be eliminated because it would give a singlet at around 1.5-2.0 ppm due to the methyl protons, but no such signal is observed. Structure III is consistent with the observed spectrum. The singlet at 2.5 ppm can be attributed to the hydrogen attached to the sulfur atom, the septet at 7.5 ppm can be attributed to the aromatic protons, and the broad signal at 8-9 ppm can be attributed to the hydrogen on the hydroxyl group. Structure IV can be eliminated because it does not have any protons attached to carbon atoms that would give rise to signals in the observed chemical shift range.

A Compound with a Molecular Formula C9H12 Has the Following

A Compound with a Molecular Formula C₉H₁₂ Has the Following