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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Propose a structure for compound E, , which has the following NMR spectral data:
Compound E Broadband-decoupled NMR: 19.1, 28.0, 70.5, 129.0, 129.8, 165.8 DEPT-90: 28.0, 129.8 DEPT-135: positive peaks at 19.1, 28.0, 129.8 ; negative peaks at 70.5, 129.0
Nitriles (RC≡N) react with Grignard reagents (R'MgBr). The reaction product from 2-methylpropanenitrile with methyl magnesium bromide has the following spectroscopic properties. Propose a structure.

MS:=86
IR: 1715
NMR: 1.05 (6 H, doublet, J 5 7 Hz); 2.12 (3 H, singlet); 2.67 (1 H, septet, J 5 7 Hz) NMR: 18.2, 27.2, 41.6, 211.2
Predict the splitting pattern for each kind of hydrogen in the following molecules:
(a)
(b)
(c) trans-2-Butene
How could you use 1H NMR to determine the regiochemistry of electrophilic addition to alkenes? For example, does addition of HCl to 1-methylcyclohexene yield 1-chloro-1-methylcyclohexane or 1-chloro-2-methylcyclohexane?
The integrated 1H NMR spectrum of a compound of the formulais shown in Figure. Propose a structure.

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