ranking these molecules according to their properties

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PodiatricADDICT

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Which is more acidic Water or phenylamide? I chose phenylamide since the if the hydrogen is removed it is more stablized right?

And also how do I calculate the reduced mass of C12-C12 and C12-C13???

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I'd also say phenylamide because the pKa of water is around 15.7 while the pKa of a typical 1* or 2* amine is around 30-35 (Hydrogens attached to O are generally more acidic than those attached to N cuz O is more electronegative than N) BUT all the resonance stabilization of the conjugate base of the amide to the carbonyl and conjugated with a benzene ring, the pKa of the phenylamide might go down to ~12. As a reference point the pKa of acetamide, which essentially is the benzene ring of phenylamide replaced with a methyl group is 17, which is already close to that of water, but the additional electron conjugation of the bezene ring will probably pull the pKa of phenylamide below 15.7.
 
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