Chem 4010/5326: Organic Spectroscopic Analysis Fall 2015 Problem Set 3 In addition to the problems assigned on the class schedule, do the following: (1) Below are the 1H and 13C NMR spectra for the four compounds shown below. (i) Assign the appropriate compound to each spectrum. (ii) Assign the resonances in each spectrum to the appropriate proton(s) or carbon(s). Assign as many as possible.

(a)

O

H2N HOHO

O

Br

(b)

(c)

(d)