Answer to Question #116239 in Organic Chemistry for Tiffany Steytler

Question

Rank the following compounds in order of increasing reactivity in electrophilic
aromatic substitution (from least to most reactive). Briefly justify your ranking.
NHCCH3 CNH2 NH2
A B C

Draw a stepwise mechanism for the following reaction and briefly explain why
this reaction will not take place in the presence of a base:

Propose a mechanism for the reaction of acetic acid with methanol in acidic
medium.

Answer 1

Electron-donor groups promote electrophilic substitution in the aromatic ring. Rank from least to most reactive is:

Mechanism for the reaction of acetic acid with methanol in acidic medium is: