Propose a structure for a compound with molecular formula

Step 1 of 2

This question presents us with a   spectrum and tells us that it belongs to a compound with molecular formula . We're asked to propose a structure that accounts for the various signals exhibited in the spectrum.

Note that the spectrum shows a singlet at 1.4 ppm that integrates to 9 protons. Signals in this region are almost always due to alkanes. The fact that there are 9 protons and that they are all equivalent (no splitting) is very indicative of a t-butyl group. This accounts for 4 carbons and 9 hydrogens, leaving us 6 carbons, 5 hydrogens, and oxygen.

There is a signal at 5 ppm that only integrates to 1 proton. Its broad nature and chemical shift is representative of an alcohol; hydrogen-bonding (intramolecular and / or intermolecular, depending on the deuterated solvent used for the NMR analysis) broadens the signal.

Therefore, we can also guess that there is a hydroxyl group present. This leaves 6 carbons and 4 hydrogens left in our unknown structure.