Chapter 13: Q 57P (page 419)
Question: The NMR spectra of compound A, , are shown. Propose a structure for A, and assign peaks in the spectra to your structure.


Short Answer

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Chapter 13: Q 57P (page 419)
Question: The NMR spectra of compound A, , are shown. Propose a structure for A, and assign peaks in the spectra to your structure.



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Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:
a.

(b)

(c)

(d)

(e)

(f)

The proton NMR spectrum is shown for a compound with the formula . The infrared spectrum displays strong bands at 1750 and 1562 and a medium-intensity band at 1320 . The normal carbon-13 and the DEPT experimental results are tabulated. Draw the structure of this compound.

Question: Propose structures for the three compounds whose NMR spectra are shown.



Propose a structure for an aromatic hydrocarbon, C11H16, that has the following 13C NMR spectral data:
Broadband decoupled: 29.5, 31.8, 50.2, 125.5, 127.5, 130.3, 139.8
DEPT-90: 125.5, 127.5, 130.3
DEPT-135: positive peaks at 29.5, 125.5, 127.5, 130.3d;negative peak at
50.2
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 .

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