Chapter 17: Q15P (page 552)
What products would you expect from oxidation of the following compounds with in aqueous acid? With the Dess-Martin periodinane?
- 1-Hexanol
- 2-Hexanol
- Hexanal
Short Answer
a.

b.

c.

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Chapter 17: Q15P (page 552)
What products would you expect from oxidation of the following compounds with in aqueous acid? With the Dess-Martin periodinane?
a.

b.

c.

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Treatment of the following epoxide with aqueous acid produces a carbocation intermediate that reacts with water to give a diol product. Show the structure of the carbocation, and propose a mechanism for the second step.
For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.
(a)

(b)

(c)

When the NMR spectrum of an alcohol is run in dimethyl sulfoxide (DMSO) solvent rather than in chloroform, exchange of the O-H proton is slow and spin-spin splitting is seen between the O-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols?
p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have pKa 5 7.15, but 3,5-dimethyl-4-nitrophenol has pKa 5 8.25. Why is 3,5-dimethyl-4- nitrophenol so much less acidic?

Identify the reagents a–f in the following scheme:

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