Problem Set 9
An alcohol has the molecular formula C6H13ClO. Look at the proton-decoupled carbon-13 spectrum below and then draw as many structural formulas that contain an OH and have the formula C6H13ClO as possible.
Now examine the APT (attached proton test) carbon-13 spectrum. In this spectrum carbons that have one or three attached hydrogens appear as downward peaks, whereas carbons that have zero or two attached hydrogens appear as positive peaks. Determine how many of each type of carbon are present.
Finally, look at the high frequency portion of the proton spectrum and try to eliminate all but one structural formula.