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Chapter 9: Q9-7P b (page 272)

How would you prepare the following carbonyl compounds starting from an alkyne (reddish-brown Br)?

b.

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01

Hydroboration – oxidation reaction

Borane adds rapidly to an alkyne resulting in vinylic borane can be oxidized by H2O2to 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.

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Most popular questions from this chapter

What products would you obtain by hydration of the following alkynes?

Synthesize the following compounds using 1-butyne as the only source of carbon along with any inorganic reagents you need. More than one step may be needed.(a) 1,1,2,2- Tetrachlorobutane(b) 1,1- Dichloro-2-ethylcyclopropane

Arrange the carbocations below in order of increasing stability.

What alkynes would you start with to prepare the following ketones?

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?

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