Question

The pKa values of ammonia, acetone, and HCN are equal to 36.0, 19.3, and 9.3, respectively. Will the following reactions take place? Explain.

(1) HCN + CH₃COONa --> NaCN + CH₃COOH

(2) (CH₃)₂CO + NaNH₂ --> CH₃COCH₂NA + NH₃

(3) CH₃COCH₂Na + CH₃COOH --> CH₃COONa + (CH₃)₂CO

Also, how many resonance structures will have acetone converted into its anion by the second reaction? Draw their electron-dot structures.

Answer 1

Acid base reactions move from Strong acid/ base to weak acid/ base

1. First reaction will not take place because CH₃COOH is more acidic than HCN.

2. Second reaction will take place as acetone is more acidic than ammonia

3. Third reaction will take place as acetic acid is more acidic than acetone.

only two resonating structures are formed from anion of acetone which are as follow