Acidity of Functional Groups

[riseNshine]

Hey guys,

There's a question in TPR that asks you to rank the acidity of cyclohexanol versus (CH3)2O and (CH3)2CO.

It was my understanding that alcohols would be most acidic, followed by esters, than the ether..However the answer said that the ester is more acidic than the alcohol. It says that the C-O and O-H dipoles are opposed but of different magnitudes resulting in a moderate dipole moment, while the C-O double bond of the ester does not have an opposing bond dipole so it dominates the large dipole moment.

^If this is true..then how come other sources online always seem to say alcohols are more acidic than esters?

Thanks!

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[polyatomic]

cyclohexanol versus (CH3)2O and (CH3)2CO

First of all, it seems to me that (CH3)2O would be an ether and (CH3)2CO would be a ketone...

Esters don't even have an acidic proton in them. Are you sure you don't mean a carboxylic acid?

 

[sdm33]

funny ha

 

[riseNshine]

oh my bad, I meant they wrote the ketones have a greater dipole moment, followed by alcohols, and then the ether

*sorry, long day of studying