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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–oxidation reaction?

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Answer:

Step by step solution

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

Using any alkyne needed, how would you prepare the following alkenes?

(a) trans-2-Octene

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

a.CH3CH2CH2C≡CH

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

Arrange the carbocations below in order of increasing stability.

Give IUPAC names for the following compounds:
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