1. Provide a complete mechanism for the following reactions. You must include all necessary steps, all curved arrows and ALL resonance structures. In addition, answer the conceptual question after the mechanism. (12 points each mechanism, 4 points per question, 32 points total)
a.
N
dilute
$H_2SO_4$
$NH_2$
In the reaction for part a, why does it stop at the amide stage and not proceed all the way to the carboxylic acid?
b.
$NH_2$
$O$
$Cl$
$AlCl_3$
$NH_2$
In the reaction for part b, why does the acyl group attach ortho to the amine and not ortho to the methyl group?
