The spectrum below goes with one of the diasteriomers shown. The other diasteriomer is t...

The spectrum below goes with one of the diasteriomers shown. The other diasteriomer is the answer to the previous question.

a. Splitting between the circled and boxed H’s below can be measured by looking at either the peak cluster of the circled H or the boxed H; however, the cluster associated with the boxed H is much harder to interpret since it is a doublet of quartets! Identify the peak cluster that goes with the circled H, and confirm that ONLY the boxed H is near enough to split this peak.

b. On which proton NMR spectrum (the one below or the one on the previous page) is the splitting between the circled and boxed H’s largest?

c. Cross out the structure below that does NOT go with the spectrum, and explain your reasoning.

d. Number or letter the H’s on the remaining structure and use these to assign each unique type of H to a cluster on the spectrum. (Note that there are some overlapping clusters near 7.4 ppm.)

e. (Check your work) The structure that you crossed out below goes with the NMR spectra on the previous page. Draw this structure on the previous page, and assign each H to a peak cluster on the proton NMR spectrum and each C to a peak on the carbon NMR spectrum.