Date on Master's Thesis/Doctoral Dissertation


Document Type

Doctoral Dissertation

Degree Name

Ph. D.



Committee Chair

Wiley, Richard H.


Nuclear magnetic resonance


The research problem presented herein involved the structural determination of several a,~-unsaturated acids and esters. The solution to this problem was sought in the nuclear magnetic resonance (n.m.r.) spectra of these compounds. The n.m.r. approach to structural problems in organic chemistry has been investigated extensively in the past ten years and it has proven to be an extremely powerful tool for this type of analysis. The data used in the structural determinations are presented in tabulated fo~, and in. the appendix tracings of the original spectra may be found. Each compound is discussed separately with respect to its probable structure and its recorded spectrum. Two brief sections follow the discussion of the spectra. One of these concerns a stereospecific solvent effect and the other relates to the effect of an anisotropic neighboring double bond on proton r -values. The configurational aSSignments for the various compounds were made possible by observing the changes in chemical shift for particular protons in different isomers and by comparison of the observed spin coupling constants with those reported in the literature. Allmost all of the compounds discussed in this thesis were of such a nature that their spectra could be interpreted on a simple first order basis. In the limited number of cases which involved more complex spectra, some approximations were attempted which made possible the assignment of configuration at several bonds. In some cases the assignments were not conclusive, but they found strong support in the approximate treatments given the complex splitting patterns.