Chapter 8: Q54a (page 262)
Question: Which of the following alcohols could notbe made selectively by hydroboration鈥搊xidation of an alkene? Explain.

Short Answer
Answer
Not possible
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Chapter 8: Q54a (page 262)
Question: Which of the following alcohols could notbe made selectively by hydroboration鈥搊xidation of an alkene? Explain.

Answer
Not possible
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Reaction of 2-methylpropene with CH3OH in the presence of H2SO4
catalyst yields methyl tert-butyl ether, CH3OC(CH3)3, by a mechanism
analogous to that of acid-catalyzed alkene hydration. Write the mechanism,
using curved arrows for each step.
Question: Which of the following alcohols could notbe made selectively by hydroboration鈥搊xidation of an alkene? Explain.

What alkenes might be used to prepare the following alcohols by hydroboration-oxidation?
Question: In planning the synthesis of one compound from another, it鈥檚 just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Dichlorocarbene can be generated by heating sodium trichloroacetate.
Propose a mechanism for the reaction, and use curved arrows to indicate
the movement of electrons in each step. What relationship does
your mechanism bear to the base-induced elimination of HCl from
chloroform?

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