Asked Dec 25, 2019

The C – H bond in acetone, (CH3)2C = O, has a pKa of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH3CH2CH3 (pKa = 50).


Expert Answer

Step 1

The pair of acid and base differing from each other by just one proton is called conjugate acid-base pair. The species formed after an acid looses electrons to a base is called conjugate base of that acid.

Step 2

The given acid is acetone.

The conjugate base of acetone is as follows.


Image Transcriptionclose

CH,—С— сн,—н. CH, —С— сн, -CHa—н — conjugate base remove Acetone

Step 3

The removal of one proton from acetone results in the formation of its conjugate base.

The delocalization of lone pair or free electrons from one atom to another is known as resonance.



Image Transcriptionclose

CH,—с— сн, CH;-C-CH2 resonance structure


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