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3. 300 MHz 1H NMR spectra in CDCl3 are shown below for five of the six isomers of dimethylphenol.

Match
each spectrum to the appropriate compound and assign the resonances of the spectrum to the appropriate
protons in the compound. (15 points)

OH OH OH OH OH OH
H6 CH3 H6 CH3 H6 CH3 CH3 CH3 H6 H2 H6 H2

H5 CH3 H5 H3 CH3 H3 H5 H3 H5 CH3 CH3 CH3


H4 CH3 H4 H4 CH3 H4
2,3-methylphenol 2,4-methylphenol 2,5-dimethylphenol 2,6-dimethylphenol 3,4-dimethylphenol 3,5-dimethylphenol

SPECTRUM A. Identify the compound (here) _____________________ and label the peaks (below) with the
corresponding proton (with labels selected among H2, H3, H4, H5, and H6 as appropriate).

5X expansion

8 7 6 5 4 3 2 1 0

SPECTRUM B. Identify the compound (here) _____________________ and label the peaks (below) with the
corresponding proton (with labels selected among H2, H3, H4, H5, and H6 as appropriate).

5X expansion

8 7 6 5 4 3 2 1 0

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.
SPECTRUM C. Identify the compound (here) _____________________ and label the peaks (below) with the
corresponding proton (with labels selected among H2, H3, H4, H5, and H6 as appropriate).

5X expansion

8 7 6 5 4 3 2 1 0

SPECTRUM D. Identify the compound (here) _____________________ and label the peaks (below) with the
corresponding proton (with labels selected among H2, H3, H4, H5, and H6 as appropriate).

5X expansion

8 7 6 5 4 3 2 1 0

SPECTRUM E. Identify the compound (here) _____________________ and label the peaks (below) with the
corresponding proton (with labels selected among H2, H3, H4, H5, and H6 as appropriate).

5X expansion

8 7 6 5 4 3 2 1 0

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.

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