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The Hydroboration-Oxidation of an Alkene to Yield 1-Octanol. 1-octene to 1-octanol using BH3-THF What might be...

The Hydroboration-Oxidation of an Alkene to Yield 1-Octanol.

1-octene to 1-octanol using BH3-THF

What might be a source of octane in the product mixture in this reaction? Hint: You did quench the hydroboration reaction with water and let the mixture sit for a week before proceeding to the oxidation step.

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Answer #1

Water is the source of octane in the product mixture in the given hydroboration-oxidation reaction.

If the reaction mixture is quenched with water after the first step (hydroboration with BH3-THF) and stand for a week, then the side reaction occurs, where octyl group (partially negative) on the borane migrates to take a proton from water to generate octane and BH2(OH) as shown below.

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