Question

In: Chemistry

Which of the following is the strongest base? CH3CH2OH CH3CH2O- CF3CH2O- CH3CH2S- CH3CH2NH- Please explain. I...

Which of the following is the strongest base?

CH3CH2OH

CH3CH2O-

CF3CH2O-

CH3CH2S-

CH3CH2NH-

Please explain. I can't find anything on this and I would really like to know how to determine this. Thanks!


Solutions

Expert Solution

CH3CH2OH. CH3CH2O- CF3CH2O- CH3CH2S- CH3CH2NH-

We all know that acidity of a molecule depends upon the donating the protons and basicity depends upon accepting the proton.

Ability to donate proton can be evaluated by Ka value. So more the Ka value more the acidic nature. Negative logarithm of Ka is pKa. So less the pKa value more acidic in nature.

More the pKa value more basic in nature.

pKa value of ethanol is 15.9 and its conjugate base is ethoxide

pKa value of CF3 CH2OH is 12.4 and its conjugate base is CF3CH2O-

pKa value of CH3CH2SH is. 10.6 and its conjugate base is CH3CH2S-

pKa value of CH3CH2NH2 is 35 and its conjugate base is CH3CH2NH-

Among the above molecules order of acidity is

thioethanol > trifloroethanol > ethanol > ethyl amine

So order of basicity of their conjugate base reverse of above order because weaker the acid stronger its conjugate base

So, CH3CH2NH-> C2H5O-> CF3CH2O->C2H5S-> C2H5OH

So strongest base is CH3CH2N- and hydrogen is hard to remove from the compound. So it is ready to accept the proton than to donate


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