Chapter 13: Q13-41E (page 419)
Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:

Short Answer
- Homotopic
- Enantiotopic
- Diastereotopic
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Chapter 13: Q13-41E (page 419)
Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:

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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.

We saw in Section 9-3 that addition of H-Br to a terminal alkyne leads to the Markovnikov addition product, with the Br bonding to the more highly substituted carbon. How could you use 13C NMR to identify the product of theaddition of 1 equivalent of H-Br to 1-hexyne?
Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:
a.

(b)

(c)

(d)

(e)

(f)

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?
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