Chapter 8: Q44Ec (page 262)
Question:Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:
Short Answer
Answer
Product of the reaction (c) is:
Chapter 8: Q44Ec (page 262)
Question:Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:
Answer
Product of the reaction (c) is:
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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.
Iodine azide, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene isused, only one product results:
a) Add lone-pair electrons to the structure shown for, and draw a
second resonance form for the molecule.
Question: Which of the following alcohols could notbe made selectively by hydroboration–oxidation of an alkene? Explain.
Question:The addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures of the carbocation intermediate to explain why none of the alternate regioisomers isformed.
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