Propose a mechanism for the acid catalyzed reaction of ethanoic acid with methylamine

Question

Propose a mechanism for the acid catalyzed reaction of ethanoic acid with methylamine

Answer 1

MeCOOH + H(+) = MeC(=O+H)OH

MeC(=O+H)OH + MeNH2 = MeC(OH)2(H2N+Me)

MeC(OH)2(H2N+Me) = H(+) + MeC(OH)2(NHMe)

MeC(OH)2(NHMe) + H(+) = MeC(HO+H)(OH)(NHMe)

MeC(HO+H)(OH)(NHMe) = MeC(=O+H)(NHMe) + H2O

MeC(=O+H)(NHMe) = H(+) + MeC(O)NHMe

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Answer 2

Methylamine is a base, ethanoic acid is an acid - you would expect and acid-base reaction to give methylammonium ethanoate. Acid catalysis in this case doesn't make sense. If a strong acid were added to the reaction mixture the methylamine would be protonated and would not react. To get the amide you need to start with the acid chloride or anhydride.