Chapter 13: Q 58P (page 419)
Question: Propose structures for the three compounds whose NMR spectra are shown.



Short Answer



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Chapter 13: Q 58P (page 419)
Question: Propose structures for the three compounds whose NMR spectra are shown.






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How could you use and1H 13C NMR to help distinguish the following
isomeric compounds of the formula C4H8?

Assume that you have a compound with the formula C3H6O .
(a) How many double bonds and/or rings does your compound
contain?
(b) Propose as many structures as you can that fit the molecular
formula.
(c) If your compound shows an infrared absorption peak at 1715cm-1,
what functional group does it have?
(d) If your compound shows a single 1H NMR absorption peak at 2.1,
what is its structure?
Assign a chemical shift to each carbon in 6-methyl-5-hepten-2-ol.
Question: 3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled with both the C1 vinylic proton (J = 16 Hz) and the C3 methylene protons (J = 8 Hz). Draw a tree diagram for the C2 proton signal, and account for the fact that a five-line multiplet is observed .

Carboxylic acids react with alcohols (R'OH) in the presence of an acid catalyst. The reaction product of propanoic acid with methanol has the following spectroscopic properties. Propose a structure.

MS: = 88
IR: 1735
NMR: 1.11 (3 H, triplet, J 5 7 Hz); 2.32 (2 H, quartet, J 5 7 Hz); 3.65 (3 H, singlet) NMR: 9.3, 27.6, 51.4, 174.6
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