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

What are the products of each aromatic substitution reaction? b.

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1
insert step 1: Identify the type of aromatic substitution reaction involved. Common types include electrophilic aromatic substitution (EAS) and nucleophilic aromatic substitution (NAS).
insert step 2: Determine the substituents on the aromatic ring and their directing effects. Activating groups (e.g., -OH, -NH2) direct incoming groups to ortho/para positions, while deactivating groups (e.g., -NO2, -CN) direct to meta positions.
insert step 3: Identify the electrophile or nucleophile involved in the reaction. In EAS, common electrophiles include halogens, nitronium ions, and sulfonyl groups. In NAS, nucleophiles such as hydroxide or amines are involved.
insert step 4: Predict the position on the aromatic ring where the substitution will occur based on the directing effects of existing substituents and the nature of the reaction.
insert step 5: Write the chemical structure of the product, showing the new substituent in the predicted position on the aromatic ring.

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Key Concepts

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

Aromatic Compounds

Aromatic compounds are cyclic structures that follow Huckel's rule, possessing a planar configuration and a continuous ring of p-orbitals, allowing for delocalized pi electrons. This delocalization imparts unique stability and reactivity characteristics, making them distinct from aliphatic compounds. Common examples include benzene and toluene.
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Electrophilic Aromatic Substitution (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction mechanism in which an electrophile replaces a hydrogen atom on an aromatic ring. This process typically involves the formation of a sigma complex (arenium ion) and is characterized by the reactivity of the aromatic system towards electrophiles, such as halogens or nitronium ions.
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Reaction Products

The products of aromatic substitution reactions depend on the nature of the electrophile and the conditions of the reaction. Common products include substituted aromatic compounds, where the hydrogen atom is replaced by the electrophile, and byproducts such as hydrogen halides in halogenation reactions. Understanding the specific conditions and reagents used is crucial for predicting the outcome.
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