hemicacetal vs ester formation

[w4nt2baDDS]

When a ketone reacts with an alcohol in acidic solution is there ever a chance for an ester to form? Or will the hemi-acetal always form instead?

If the hemi-acetal does in fact always form, then how does a ketone become an ester? Only with MCPBA/RCOOOH?

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[DAT Destroyer]

A ketone will react with a mole of alcohol to produce a hemiacetal......if 2 moles are used, we make an acetal. Consult any text to see these mechanisms..... There are a few ways to get a ketone to the ester.....MCPBA via a Baeyer Villiger reaction is one of them......or perhaps if it is a methyl ketone, we can employ a haloform reaction to get the carboxy acid. The acid then can be made into the acyl halide and allowed to react with the corresponding alcohol.

Hope this helps.

Dr. Jim Romano

 

[w4nt2baDDS]

Thanks! That clears a few things up for me.

 

[DAT Destroyer]

Thanks! That clears a few things up for me.

Great!