Active-learning Questions (completed individually)

1. Provide the general electrophilic aromatic substitution (EAS) reaction, as well as all the specific EAS reactions of benzene. Provide the general mechanism for this reaction including all the resonance structures of the arenium ion. Name the steps of the mechanism.
2. Provide the major product formed when benzene reacts with 1-chloro-2-methylpropane in the presence of aluminum trichloride. Provide the mechanism for this reaction. Solved problem 15.2 is important.
3. Synthesize pentylbenzene from benzene and pentanoyl chloride. Provide the names of the electrophilic aromatic substitution reactions used. Problem 15.5 (A and B) is important. 
4. Substituents attached to a benzene ring may be classified as either electron-donating or as electron-withdrawing groups. Prepare a circle diagram (example below) for each group.

Portfolio Questions (completed individually)

5. Following the examples given in the solved problem 15.4, as well as the practice problems 15.7, 15.11, 15.12, 15.20 and 15.21, predict the products formed after each step of the following reaction sequences.  If the final product would be a mixture of ortho and para isomers, you should state so.  In addition, if possible, state which of these isomers is the major one.

a	Biphenyl (phenylbenzene) is chlorinated
b	Benzophenone reacts with 1-chloropropane in the presence of AlCl3 (cat.)
c	p-Chloroacetophenone is nitrated
d	3-Chlorobenzoic acid is brominated
e	4-Acetoxybiphenyl is sulfonated
f	N-Phenylbenzamide (benzanilide) is brominated
g	4-Methoxybenzaldehyde reacts ethanoyl chloride in the presence of AlCl3(cat.), followed by an acidification step with H3O+
h	Starting with phenol give the product(s) after the following series of reactions 1) acetyl chloride, HO- 2) Cl2/FeCl3 (cat.) 3) H3O+/ heat 4) HO-
i
j	Provide products A, B and C in the following reaction sequence:

6. Taking into consideration the use of a blocking group, synthesize 2,6-dichlorobenzoic acid starting from benzene. You may use any single-carbon containing compound without synthesizing it.  Provide the names of the electrophilic aromatic substitution reactions used in the synthesis.  Explain your strategy. Problem 15.15 is important, as well as the synthetic schemes on page 691.
7. Taking into consideration the use of a protecting group, synthesize 2-chloro-4-propylphenol starting from phenol. You may use compounds containing one (1) to four (4) carbon atoms without synthesizing them. Provide the names of the electrophilic aromatic substitution reactions used in the synthesis. Explain your choice of strategy. Note that problem 15.7 on page 679 is important.