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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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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

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

What products would you expect from the following reactions?

a. CH3CH2CH2C鈮�CH+Cl2

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

a.CH3CH2CH2C鈮�CH

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

step is needed.

A hydrocarbon of unknown structure has the formula C8H10. On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of H2 is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of H2 are absorbed.

(a) How many degrees of unsaturation are present in the unknown structure?

(b) How many triple bonds are present?

(c) How many double bonds are present?

(d) How many rings are present?

(e) Draw a structure that fits the data.
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