Chapter 25: 76 (page 1048)
Draw the product Y of the following reaction sequence. Y was an intermediate in the remarkable synthesis of cyclooctatetraene by Wilstatter in 1911.

Short Answer

Mechanism of the given reaction
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Chapter 25: 76 (page 1048)
Draw the product Y of the following reaction sequence. Y was an intermediate in the remarkable synthesis of cyclooctatetraene by Wilstatter in 1911.


Mechanism of the given reaction
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Question: Give a systematic or common name for each compound.


Question: Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, 鈥淓cstasy鈥) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.

What amine is formed by reduction of each amide?
a.
b.

c.

Question: Which amines cannot be prepared by a Gabriel synthesis? Explain your choices.
a.

b.

c.

d.

Tertiary ( ) aromatic amines react with and HCl to afford products of electrophilic aromatic substitution. Draw a stepwise mechanism for this nitrosation reaction and explain why it occurs only on benzene rings with strong ortho, para activating groups.

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