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: