Chapter 12: PROBLEM 12.25 (page 480)
Question: What carbonyl compound is formed when each alcohol is treated with HCrO4––Amberlyst A-26 resin?
a.

b.

c.

Short Answer
Answer
a.

b.

c.

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Chapter 12: PROBLEM 12.25 (page 480)
Question: What carbonyl compound is formed when each alcohol is treated with HCrO4––Amberlyst A-26 resin?
a.

b.

c.

Answer
a.

b.

c.

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Question: Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula , both yield 2,6-dimethyloctane when treated with and a Pd catalyst. Ozonolysis of oximene forms , , and . Ozonolysis of myrcene yields , (two equiv), and . Identify the structures of oximene and myrcene.
Question: Identify A in the following reaction sequence and draw a mechanism for the conversion of A to B. B has been converted to (S,S)-reboxetine, an antidepressant marketed outside the United States.

Question: Draw the organic products formed in each reaction.
a.

b.

c.

d.

Question: What allylic alcohol and DET isomer are needed to make each chiral epoxide using a sharpless asymmetric epoxidation reaction?
Question: In the oxidation of cyclohexanols, it is generally true that sterically hindered alcohols react faster than unhindered alcohols. Which of the following alcohols should be oxidized more rapidly?

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