Chapter 18: Q24E (page 594)
Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

Short Answer
a.

b.

c.

d.

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Chapter 18: Q24E (page 594)
Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

a.

b.

c.

d.

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How would you prepare the following ethers?

2-Butene-1-thiol is one component of skunk spray. How would you synthesize this substance from methyl 2-butenoate? From 1,3-butadiene?

Griginard reagents react with oxetane, a four membered cyclic ether, to yield primary alcohols, but the reaction is much slower than the corresponding reaction with ethylene oxide. Suggest a reason for the difference in reactivity between oxetane and ethylene oxide.

Oxetane
Acid-catalyzed hydrolysis of a 1,2-epoxycyclohexane produces a transdiaxial 1,2-diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-1,2-epoxycyclohexane? (Recall that the bulky tert-butyl group locks the cyclohexane ring into a specific conformation.)
How would you synthesize anethole (Problem 18-54) from phenol?
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