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Peter Norris, Ph.D.
 
Structure unknowns using 1H, 13C, IR, and MS spectra

In these problems you are given the molecular formula of the unknown and then at least the H NMR spectrum from which you should be able to work out a structure. As the molecules get more complicated you are given C NMR data, as well as IR and Mass spectra in many cases.

         Unknowns        Formula

Unknown 01 C2H3Cl3
Unknown 02 C2H4Cl2
Unknown 03 C4H10O
Unknown 04 C3H8O
Unknown 05 C8H8O
Unknown 06 C5H10O
Unknown 07 C3H9N
Unknown 08 C4H10O
Unknown 09
C4H11N
Unknown 10
C7H6O
Unknown 11
C15H14O
Unknown 12
C13H10O
Unknown 13
C8H8O
Unknown 14
C7H5ClO
Unknown 15 C5H10O
Unknown 16 C14H10O2
Unknown 17
C13H12O
Unknown 18 C6H10O
Unknown 19 C5H8O2
Unknown 20
C14H28O2
Unknown 21
C8H8O2

Answers for 9-21 are here

Honors 719-721 Organic Chemistry by Chris Gabriel, Adam Freeman, and Alok Makam.

Thanks to the NMR archive at Pacific Lutheran University for some of the 1H and 13C NMR data and the NIST Webbook for some of the IR and Mass spectral data ("IR and Mass Spectra" by NIST Mass Spec Data Center, S.E. Stein, director, NIST Standard Reference Database Number 69, Eds. W.G. Mallard and P.J. Linstrom, August 1997, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).

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