Chapter 8: Q54d (page 262)
Question: Which of the following alcohols could notbe made selectively by hydroboration–oxidation of an alkene? Explain.
Answer
Not possible
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Which of the reactions below would result in a product mixture thatwould rotate plane-polarized light?
b)
Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis- and trans-1-bromo-3-methylcyclohexane and cis- and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1,2-dibromocyclohexane as the sole product. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.
Hydroxylation of cis-2-butene with yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference between them.
Using an oxidative cleavage reaction, explain how you would distinguish between the following two isomeric dienes:
What products would you expect from oxymercuration-demercuration of the following alkenes?
a)
b)
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