What happens when ethanol is treated with methyl magnesium bromide and the product is hydrolysed?
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We get ethanol, methane, and bromomagnesium hydroxide as shown in the equation
H3CMgBr+HOEt→MeH↑+MgBr++−OEtH3CMgBr+HOEt→MeH↑+MgBr++−OEt
Hydrolysis would give the alcohol.
Of course, normally you would carefully protect a Grignard reagent from protic sources,but you might want (for a separate experiment) an ALKANE labelled with a deuterium nucleus.
H3CMgBr+D2O→MeD↑+MgBr++−ODH3CMgBr+D2O→MeD↑+MgBr++−OD
And so you would use heavy water or ethanol−d1ethanol−d1to label the methane.
H3CMgBr+HOEt→MeH↑+MgBr++−OEtH3CMgBr+HOEt→MeH↑+MgBr++−OEt
Hydrolysis would give the alcohol.
Of course, normally you would carefully protect a Grignard reagent from protic sources,but you might want (for a separate experiment) an ALKANE labelled with a deuterium nucleus.
H3CMgBr+D2O→MeD↑+MgBr++−ODH3CMgBr+D2O→MeD↑+MgBr++−OD
And so you would use heavy water or ethanol−d1ethanol−d1to label the methane.
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