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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: brasarehot on October 26, 2010, 11:00:16 AM

Title: What does H2O2, NaOH do in this reaction?
Post by: brasarehot on October 26, 2010, 11:00:16 AM

Cyclohexanone to 1-cyclohexyl 1-pentanol. 1) (C6H5)3P=CHCH2CH2CH2CH3; 2) BH3, THF; 3) H2O2, NaOH.
It seems to me you get the product after BH3, so why is H2O2 there?

Title: Re: What does H2O2, NaOH do in this reaction?
Post by: discodermolide on October 26, 2010, 11:13:57 AM

Quote from: brasarehot on October 26, 2010, 11:00:16 AM

Cyclohexanone to 1-cyclohexyl 1-pentanol. 1) (C6H5)3P=CHCH2CH2CH2CH3; 2) BH3, THF; 3) H2O2, NaOH.
It seems to me you get the product after BH3, so why is H2O2 there?

This is a classical hydroboration of a double bond, which requires oxidation of the borinic acid ester intermediate, take it from there

Title: Re: What does H2O2, NaOH do in this reaction?
Post by: orgopete on October 28, 2010, 11:09:07 PM

Role of H2O2, see mechanism here: http://orgo.curvedarrow.com/punbb/viewtopic.php?id=336