Overview
CHEM 205 Worksheet (WS8)
38 Points Total
Key Topics: 1H NMR, IR, and Structural Elucidation
1. (22pts) (a) Rank each proton shown below in terms of relative chemical shift in the 1H NMR spectrum.
(1 = most upfield, 3 = most downfield) (1pt for each correct ranking)
(b) For each separate compound below determine the theoretical number of peaks one would predict to see
in the 1H NMR spectra. Write the corresponding number in the empty boxes below each structure. (2pts
for each correct answer)
(c) Each of the following compounds below are characterized by a 1H NMR spectrum that consists of only
a single peak having the chemical shift indicated. Identify and draw a bond-line structure for each
compound, respectively. (4pts for each correct answer)
(i) C2H3Cl3 – at ~ 2.7 ppm (ii) C5H10 – at ~ 1.5 ppm