In the previous post, we discussed the ring-opening reactions of epoxides with strong and weak nucleophiles. Using this information, try solving the following practice problems.
Reactions of Epoxides Practice Problems
Practice
1.
a)
Determine the structure of epoxides, including the stereochemistry, that are formed in each reaction.
Answer
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Answer
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Answer
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2.
a)
Identify the reactants that you would use to prepare each of the following epoxides.
Answer
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Answer
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Answer
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Answer
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Answer
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3.
a)
Draw the curved arrow mechanism to predict the product in each reaction.
Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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4.
a)
Determine the reactants in the correct order that will allow you to achieve these synthetic transformations.
Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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5.
Identify the missing reagents and products in the following synthetic scheme:
Answer
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6.
Draw a plausible mechanism for the following synthesis:
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7.
Propose a mechanism for the following synthesis and determine if the final product is aromatic or not:
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8.
Draw a plausible mechanism for the following synthetic transformation:
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9.
Propose a mechanism for the formation of products A and B in the following Friedel-Crafts acylation reactions:
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10.
When the following cyclohexenes are brominated different configurational isomers are obtained. How would you explain the stereochemistry of these reactions?
Note: Tetraethylammonium bromide (Et4NBr) is a source of Br– ion.
Answer
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11.
When the following epoxide is treated with acetic acid (AcOH), a product is formed with a cis configuration of the OH and Ph groups. The OH and Ph groups are in trans configuration when triflic acid (TfOH) is used. How can the configuration of the products be explained?
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12.
Propose a mechanism for the following ring-opening reaction of cyclopropane:
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