This document contains an assignment on benzene and aromatic compounds. It instructs students to draw the structures of various substituted benzenes, outline the mechanism for forming isopropylbenzene from propene and benzene, predict major products of electrophilic aromatic substitutions, identify if compounds are aromatic or antiaromatic, and list characteristics of aromatic compounds. The assignment contains questions on drawing structures, outlining reaction mechanisms, predicting products, and identifying aromatic properties.

1. EP101 / EG101 Jan-April 2010
Assignment 6: Benzene & Aromatic Compound
1. Draw the structure for each of the following:
a. p-bromotoulene
b. 1-bromo-2-neo-pentylbenzene
c. m-dinitrobenzene
d. tert-butylbenzene
e. benzyl bromide
2. Outline all steps in a reasonable mechanism for formation of isopropylbenzene from propene
and benzene in liquid HF. Your mechanism must encounter for the product being
isopropylbenzene, not propylbenzene.
3. Based on the effect of substituent on electrophilic aromatic substitution, predict the major
product form when: (you need to show all the mechanism of the reaction, especially the
resonance effect structure)
a. toluene is sulfonated
b. nitrobenzene is brominated
c. phenol is subjected to friedel craft acetyl chloride
4a. There are 2 compound shown below, explain which one is aromatic and antiaromatic
compound.
(i) (ii)
b. List out all the special characteristic of an aromatic compound.
Ms Tan Jully School of Eng., UCSI University