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Ch.22 - Organic Chemistry
Chapter 22, Problem 69a

What are the products of each aromatic substitution reaction? a.
Benzene reacting with bromine in the presence of FeBr3 to illustrate aromatic substitution.

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1
Identify the type of reaction: This is an example of an electrophilic aromatic substitution reaction.
Recognize the reactants: Benzene (C6H6) and bromine (Br2) in the presence of a catalyst, FeBr3.
Understand the role of the catalyst: FeBr3 helps to generate the electrophile, Br+, by polarizing the Br2 molecule.
Determine the electrophile: The electrophile in this reaction is the bromonium ion (Br+).
Predict the product: The bromonium ion (Br+) will substitute one of the hydrogen atoms on the benzene ring, resulting in bromobenzene (C6H5Br) as the product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Aromatic Substitution

Aromatic substitution is a chemical reaction where an atom, typically hydrogen, in an aromatic compound is replaced by another atom or group. This process preserves the aromaticity of the compound, meaning the stability and electron delocalization of the aromatic ring remain intact. Common examples include electrophilic aromatic substitution, where an electrophile attacks the aromatic ring.
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Electrophilic Aromatic Substitution (EAS)

Electrophilic aromatic substitution (EAS) is a specific type of aromatic substitution where an electrophile reacts with an aromatic compound. In the presence of a catalyst, such as FeBr3, the electrophile (like Br+) is generated from a halogen source (Br2), allowing it to replace a hydrogen atom on the aromatic ring. This reaction is crucial for synthesizing various aromatic compounds.
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Catalysts in EAS

Catalysts, such as FeBr3 in the given reaction, are substances that increase the rate of a chemical reaction without being consumed in the process. In EAS, catalysts help generate a more reactive electrophile from a less reactive halogen molecule, facilitating the substitution reaction. They play a vital role in making the reaction more efficient and selective.
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