Problem: Disiamytborane (shown as R2BH) adds to a triple bond to give an alkenylborane. Upon oxidation with -OH, H2O2, the alkenylborane will form an enol that tautomerizes to an aldehyde. In the first box below, draw the mechanism arrows for the reaction of disiamylborane with the alkyne, and in the last box draw the structure of the aldehyde.

FREE Expert Solution

Reaction 1

  • Hydroboration
  • Electrophilic Addition

Reaction 2 

  • Oxidation


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Problem Details

Disiamytborane (shown as R2BH) adds to a triple bond to give an alkenylborane. Upon oxidation with -OH, H2O2, the alkenylborane will form an enol that tautomerizes to an aldehyde. In the first box below, draw the mechanism arrows for the reaction of disiamylborane with the alkyne, and in the last box draw the structure of the aldehyde.

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Alkyne Hydroboration concept. You can view video lessons to learn Alkyne Hydroboration. Or if you need more Alkyne Hydroboration practice, you can also practice Alkyne Hydroboration practice problems.