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Chapter 9: Q9-6P (page 271)

What alkyne would you start with to prepare each of the following compounds by a hydroboration鈥搊xidation reaction?

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01

Hydroboration – oxidation reaction

Borane adds rapidly to an alkyne resulting in vinylic borane can be oxidized by to yield an enol. Tautomerization then gives either a ketone or an aldehyde.

  • The terminal alkyne leads to the formation of aldehyde
  • The internal alkyne leads to the formation of ketone
02

 Formation of compound a

Terminal alkyne undergoes two additions, giving a doubly hydroborated intermediate. Oxidation with H2O2replaces both boron atoms with oxygen and generates the aldehyde.

03

 Formation of compound b

Internal alkyne undergoes two additions, giving a doubly hydroborated intermediate. Oxidation with H2O2 replaces both boron atoms with oxygen and generates ketone.

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Most popular questions from this chapter

How would you carry out the following conversions? More than one

step is needed in each case.

Which of the following bases could be used to deprotonate 1-butyne?

(a)

A cumulene is a compound with three adjacent double bonds. Draw an orbital picture of a cumulene. What kind of hybridization do the two central carbon atoms have? What is the geometric relationship of the substituents on one end to the substituents on the other end? What kind of isomerism is possible? Make a model to help see the answer.

R2C=C=C=CR2

A cumulene

Question: How would you carry out the following conversions? More than one

step may be needed in some instances.

The sex attractant given off by the common housefly is an alkene named muscalure. Propose a synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure?

Muscalure
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