3.

The 1H NMR spectrum of (S)-glycidyl benzyl ether (300 MHz in CDCl3, with TMS) is shown below, along
with expansions of the resonances at 4.6, 3.7, 3.4, 3.2, 2.8, and 2.6 ppm. (20 points)
O
O
(S)-glycidyl benzyl ether

0 ppm

4.6 ppm
3.4 ppm

3.7 ppm

10

20

30

40 Hz

10

20 Hz

10

20 Hz

20 Hz

2.6 ppm

2.8 ppm

3.2 ppm

10

10

20 Hz

10

20 Hz

a. Assign the resonances at 4.6, 3.7, 3.4, 3.2, 2.8, and 2.6 ppm to the various protons in the molecule, by writing
the chemical shift next to the prottons on the diagram below. Appendix F from Silverstein is provided at the end
of this problem to help you.
H H

H H

b. Describe the multiplets and measure the coupling constants for the resonances at 3.7, 3.4, 2.8, and 2.6 ppm:
3.7 ppm (description and coupling constants): __________________________
3.4 ppm (description and coupling constants): __________________________
2.8 ppm (description and coupling constants): __________________________
2.6 ppm (description and coupling constants): __________________________
This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
Spectra are from Sigma-Aldrich (www.sigmaaldrich.com) under fair use.

c. Explain the appearance of the resonances at 4.6 ppm:

d. Based on your analysis in sections ac, write each geminal (2JHH) or vicinal (3JHH) coupling constant on the
line by the corresponding arrow.
Hz
Hz

Hz

Hz

Hz
Hz

H
H

BnO

Explain the appearance of the resonances at 3.2 ppm. Make a splitting diagram to aid in your explanation. Use a
scale of 1 box is equal to 1 Hz on the horizontal axis and accurately represent the relative heights of the lines on
the vertical axis.

e. What differences would you expect between the 1H NMR spectrum of (R)-glycidyl benzyl ether and the 1H
NMR spectrum of (S)-glycidyl benzyl ether?

f. What differences would you expect between the 1H NMR spectrum of racemic glycidyl benzyl ether and the
H NMR spectrum of (S)-glycidyl benzyl ether?

This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
Spectra are from Sigma-Aldrich (www.sigmaaldrich.com) under fair use.

This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
Spectra are from Sigma-Aldrich (www.sigmaaldrich.com) under fair use.