Question

Draw a mechanism for the reaction of methylamine with 2-methylpropanoic acid. Draw any necessary curved arrows. Show the products of the reaction. Include any nonzero formal charges and all lone pairs of electrons. Indicate which side of the reaction is favored at equilibrium.

Answer 1

See figure 1

Step-by-step explanation:

On this case we have a base (methylamine) and an acid (2-methyl propanoic acid). When we have an acid and a base an acid-base reaction will take place, on this specific case we will produce an ammonium carboxylate salt.

Now the question is: ¿These compounds can react by a nucleophile acyl substitution reaction? in other words ¿These compounds can produce an amide?

Due to the nature of the compounds (base and acid), the nucleophile (methylamine) doesn't have the ability to attack the carbon of the carbonyl group due to his basicity. The methylamine will react with the acid-producing a positive charge on the nitrogen and with this charge, the methylamine loses all his nucleophilicity.

I hope it helps!