I think I'm doing it correctly but perhaps I'm missing something? Do they both need to be protonated enter image description here

  • $\begingroup$ i don't think they are both protonated because I tried that and it still came out to be wrong? $\endgroup$ – Harry Johnson Mar 22 '14 at 22:04
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    $\begingroup$ You were missing something, but your comment shows that you're thinking in the right direction! $\endgroup$ – Klaus-Dieter Warzecha Mar 22 '14 at 22:27
  • $\begingroup$ @KlausWarzecha I let the carboxylic be a salt and put in NH3CH3(+) and it still is wrong? What am I doing wrong ? $\endgroup$ – Harry Johnson Mar 22 '14 at 22:33

We agree that the amide is cleaved :)

Is it conceivable that methylamine, which is a gas under standard conditions, exists as methylammonium chloride here? ;)

$\ce{H3CCH2-CONHCH3 +HCl +H2O -> CH3CH2COOH + CH3NH3+Cl-}$


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