You synthesized 6,7-epoxygeraniol (structure below). Which peaks in the H-NMR would have the largest change in chemical shift? Be sure to state the peak, and the expected shift (e. g. shift upfield, downfield, to a particular range, etc…)
Homework Answers
Structure of geraniol:
Structure of 6,7-epoxygeraniol:
The peak of hydrogen atom marked in red will be shifted upfield after epoxidation of geraniol. In geraniol, the chemical shift of that hydrogen will be in the range of 5 - 6 ppm due to the deshielding effect of the olefinic double bond. After the epoxidation of the double bond, the new chemical shift of that marked hydrogen atom will be in the range of 3 - 4 ppm. Therefore, for that marked hydrogen atom, the change in chemical shift is ~ 2 ppm.
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You synthesized 6,7-epoxygeraniol (structure below). Which peaks in the H-NMR would have the larg...
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