Question

4.15 Predict the products of the following reaction. CI AICI$_3$ (Hint: There should be a mixture of multiple products in this case. Be sure to consider all of the possible rearrangements that can take place. If you are rusty on carbocation rearrangements, then you should go back and review them now.) 84 CHAPTER 4 ELECTROPHILIC AROMATIC SUBSTITUTION 4.16 On a separate piece of paper, draw a mechanism of formation for each one of the three prod- ucts from the previous problem. 4.17 On a separate piece of paper, draw a mechanism for the following transformation. Make sure to show the mechanism of formation of the acylium ion that reacts with the ring: CI AICI$_3$ Friedel-Crafts reactions have a few limitations. You should take a moment to read about them in your textbook. The two most important limitations are as follows: 1. When performing a Friedel-Crafts alkylation, it is often difficult to install just one alkyl group. Each alkyl group makes the ring more reactive toward a subsequent attack on the same ring. 2. When performing a Friedel-Crafts acylation, it is generally not possible to install more than one acyl group. The presence of one acyl group makes the ring less reactive toward a second acylation. We need to understand WHY an alkyl group makes the ring more reactive, and WHY an acyl group makes the ring less reactive. We will explain this in greater detail during the upcoming sections. But first, we have one more electrophile to discuss.

          4.15 Predict the products of the following reaction.
CI
AICI$_3$
(Hint: There should be a mixture of multiple products in this case. Be sure to consider all of the
possible rearrangements that can take place. If you are rusty on carbocation rearrangements,
then you should go back and review them now.)
84 CHAPTER 4 ELECTROPHILIC AROMATIC SUBSTITUTION
4.16 On a separate piece of paper, draw a mechanism of formation for each one of the three prod-
ucts from the previous problem.
4.17 On a separate piece of paper, draw a mechanism for the following transformation. Make sure
to show the mechanism of formation of the acylium ion that reacts with the ring:
CI
AICI$_3$
Friedel-Crafts reactions have a few limitations. You should take a moment to read about them in your
textbook. The two most important limitations are as follows:
1. When performing a Friedel-Crafts alkylation, it is often difficult to install just one alkyl group.
Each alkyl group makes the ring more reactive toward a subsequent attack on the same ring.
2. When performing a Friedel-Crafts acylation, it is generally not possible to install more than
one acyl group. The presence of one acyl group makes the ring less reactive toward a second
acylation.
We need to understand WHY an alkyl group makes the ring more reactive, and WHY an acyl group
makes the ring less reactive. We will explain this in greater detail during the upcoming sections. But
first, we have one more electrophile to discuss.

4.15 Predict the products of the following reaction.
CI
AICI3
(Hint: There should be a mixture of multiple products in this case. Be sure to consider all of the
possible rearrangements that can take place. If you are rusty on carbocation rearrangements,
then you should go back and review them now.)
84 CHAPTER 4 ELECTROPHILIC AROMATIC SUBSTITUTION
4.16 On a separate piece of paper, draw a mechanism of formation for each one of the three prod-
ucts from the previous problem.
4.17 On a separate piece of paper, draw a mechanism for the following transformation. Make sure
to show the mechanism of formation of the acylium ion that reacts with the ring:
CI
AICI3
Friedel-Crafts reactions have a few limitations. You should take a moment to read about them in your
textbook. The two most important limitations are as follows:
1. When performing a Friedel-Crafts alkylation, it is often difficult to install just one alkyl group.
Each alkyl group makes the ring more reactive toward a subsequent attack on the same ring.
2. When performing a Friedel-Crafts acylation, it is generally not possible to install more than
one acyl group. The presence of one acyl group makes the ring less reactive toward a second
acylation.
We need to understand WHY an alkyl group makes the ring more reactive, and WHY an acyl group
makes the ring less reactive. We will explain this in greater detail during the upcoming sections. But
first, we have one more electrophile to discuss.

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