Chem 336 - Spring 2000
Organic Chemistry III
Dr. Carl C. Wamser

Chapter 20 Challenge Question

Challenge problem:

An old method for determining whether a disubstituted benzene was ortho, meta, or para was to perform a nitration and count the number of different mononitration products that could be isolated.

a) Apply this to the three dichlorobenzenes and indicate how the method could distinguish them.
b) Does the method work with bromochlorobenzenes?
c) Does the method work with chloronitrobenzenes?
d) This method does involve an assumption about nitration reactions and substituent effects. What is it?