Styrene to 2-phenylethanol?

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popstar
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Styrene to 2-phenylethanol?

Post by popstar »

Hi I did a reaction for an organic chemistry lab that was a hydroboration-oxidation of styrene using borane dimethylsulfide and THF as the solvents, then hydrogen peroxide and NaOH, to produce 2-phenylethanol. I cannot figure out how to balance this reaction, due to the solvents, but I have refreshed myself on stoichiometry. Can anybody help?
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ChenBeier
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Post by ChenBeier »

The boran will add to the vinyl doublebond of styrene and build the Anti Markovnikov product. You have 2-Phenyl-ethylboran. With Peroxid you can oxidise it and get the alcohol.

C6H5-CH=CH2 + BH3(CH3)2S => C6H5-CH2-CH2-BH2 + (CH3)2S

C6H5-CH2-CH2-BH2 + 3 H2O2 + 3 OH- => C6H5-CH2-CH2-OH + BO3 3- + 5 H2O
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