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Unformatted text preview: Chemistry 14C Spring 2009 Lecture 2 Exam 2 Solutions Page 1 Statistics : High score, average, and low score will be posted on the course web site after exam grading is complete. The exam is ready to be picked up when these numbers are posted. Some questions have more than one answer, even though only one answer may be listed here. To see the projected course grade cutoffs, consult the grading scale on the Chemistry 14C course web page. 1. 282 2. (a) 20.5 (b) 0.5 3. A base peak. Beyond this we cannot determine if the most abundant ion is a molecular ion or a fragment ion . 4. Oleic acid 5. The 1 H-NMR spectrum of oleic acid has 1 singlet, 0 doublets, and 17 signals with splitting more complex than a doublet. 6. The 1 H-NMR spectrum of oleic acid has 3 signals of integral = 1, 14 signals of integral = 2, and 1 signal whose integral is more than 2. 7. The 1 H-NMR spectrum of oleic acid has 3 signals whose chemical shift is 5.0 or more, and 0 signals more shielded than TMS. Chemical shift > 5.0 signals are RCOO H and the two vinyl protons. No signals have a chemical shift of less than zero . 8. Oleic acid has 3 hydrogens that are not equivalent to any other hydrogens within the molecule. The COOH and vinyl hydrogens . 9. Oleic acid and linoleic acid. Check the characteristic chemical shift for carboxylic acid protons . 10. The 13 C-NMR spectrum of oleic acid has 1 singlet when broadband decoupling is not used, and 18 singlets when broadband decoupling is used. In addition, this 13 C-NMR spectrum has 1 signal whose chemical shift is 160 ppm or more....
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