Chapter 13: Q13-12P (page 404)
Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:
a.

(b)

(c)

(d)

(e)

(f)

Short Answer
- Homotopic
- Enantiotopic
- Homotopic
- Diastereotopic
- Homotopic
- homotopic
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Chapter 13: Q13-12P (page 404)
Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:
a.

(b)

(c)

(d)

(e)

(f)

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Long-range coupling between protons more than two carbon atoms apart is sometimes observed when p bonds intervene. An example is found in 1-methoxy-1-buten-3-yne. Not only does the acetylenic proton, , couple with the vinylic proton , it also couples with the vinylic proton , four carbon atoms away. The data are:

Construct tree diagrams that account for the observed splitting patterns of ,, and .
Compound F, a hydrocarbon with = 96 in its mass spectrum, undergoes reaction with HBr to yield compound G. Propose structures for F and G, whose NMR spectral data are given below.
a. Compound F Broadband-decoupled NMR: 27.6, 29.3, 32.2, 132.4 d DEPT-90: 132.4 d DEPT-135: positive peak at 132.4 d; negative peaks at 27.6, 29.3, 32.2 d
b. Compound G Broadband-decoupled NMR: 25.1, 27.7, 39.9, 56.0 d DEPT-90: 56.0 d DEPT-135: positive peak at 56.0 d; negative peaks at 25.1, 27.7, 39.9 d
How many absorptions would you expect to observe in the NMR
spectra of the following compounds?
(a) 1,1-Dimethylcyclohexane
(b) CH3CH2OCH3
(c) tert-Butylcyclohexane
(d) 3-Methyl-1-pentyne
(e) cis-1,2-Dimethylcyclohexane
(f) Cyclohexanone
How many 13C NMR absorptions would you expect for cis-1,3-dimethylcyclohexane?For trans-1,3-dimethylcyclohexane? Explain.
How many kinds of electronically non-equivalent protons are present in each of the following compounds, and thus how many NMR absorptions might you expect in each?
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