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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

The following cycloalkyne is too unstable to exist. Explain

What products would you expect from the following reactions?

b.

How would you carry out the following reactions to introduce deuterium into organic molecules?

(a)

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c.

d.

1-Octen-3-ol, a potent mosquito attractant commonly used in mosquito traps, can be prepared in two steps from hexanal, CH3CH2CH2CH2CH2CHO . The first step is an acetylide-addition reaction like that described in Problem 9-50. What is the structure of the product from the first step, and how can it be converted into 1-octen-3-ol?

Give IUPAC names for the following compounds:
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