Chapter 14: Q.21558-14-9P. (page 538)
For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.
a.

b.

c.

Short Answer
a.

b.

c.

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Chapter 14: Q.21558-14-9P. (page 538)
For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.
a.

b.

c.

a.

b.

c.

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Question: How many 1H NMR signals does each natural product exhibit?
a.

b.

c.

d.

Label the protons in each highlighted CH2 group as enantiotopic, diastereotopic, or homotopic.
a.

b.

c.

Compound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?

Question: How many 13C NMR signals do each compound exhibit?
Which compounds give a 1H NMR spectrum with two signals in a ratio of 2:3?
a.

b.

c.

d.

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