Chapter 13: Q13-14P (page 404)
How many absorptions would you expect (S)-malate, an intermediate in carbohydrate metabolism, to have in itsspectrum? Explain.

Short Answer
The signal given by S-malate is 6.
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Chapter 13: Q13-14P (page 404)
How many absorptions would you expect (S)-malate, an intermediate in carbohydrate metabolism, to have in itsspectrum? Explain.

The signal given by S-malate is 6.
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Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:
a.

(b)

(c)

(d)

(e)

(f)

Propose structures for compounds that fit the following 1H NMR data:
a.
2.18(3H, singlet)
4.16(2H, doublet j=7Hz)
5.71(1H, triplet j=7Hz)
b.
1.30(9H, singlet)
7.30(5H, singlet)
c.
2.11(3H, singlet)
3.52(2H, triplet j=6Hz)
5.71(2H, triplet j=6Hz)
d.
2.15(2H, quintent j=7Hz)
2.75(2H, triplet j=7Hz)
3.38(2H, triplet j=7Hz)
7.22(5H, singlet)
Question: When measured on a spectrometer operating at 200 MHz, chloroform shows a single sharp absorption at 7.3.
(a)How many parts per million downfield from TMS does chloroform absorb?
(b)How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz?
(c)What would be the position of the chloroform absorption inunits when measured on a 360 MHz spectrometer?
Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:
a.

b.

c.

3-Methyl-2-butanol has five signals in its NMR spectrum at 17.90, 18.15, 20.00, 35.05, and 72.75 d. Why are the two methyl groups attached to C3 non- equivalent? Making a molecular model should be helpful.

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