Predict the products of the following reactions:
(c)

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Step 1: Analyze the starting material. The molecule is a nitroaniline, specifically 2-nitroaniline, with an amino group (-NH₂) at the ortho position relative to the nitro group (-NO₂) on a benzene ring.

Step 2: Understand the reaction conditions. The first step involves sodium nitrite (NaNO₂) and hydrochloric acid (HCl), which are used to convert the amino group (-NH₂) into a diazonium salt (-N₂⁺Cl⁻). This is known as diazotization.

Step 3: Write the intermediate structure. After diazotization, the amino group is replaced by a diazonium group (-N₂⁺Cl⁻), resulting in 2-nitrobenzenediazonium chloride.

Step 4: Examine the second reagent, CuBr. Copper(I) bromide (CuBr) facilitates a Sandmeyer reaction, where the diazonium group (-N₂⁺Cl⁻) is replaced by a bromine atom (-Br). This substitution occurs via a radical mechanism.

Step 5: Predict the final product. The bromine atom replaces the diazonium group, yielding 2-nitrobromobenzene as the final product. The nitro group (-NO₂) remains unchanged during the reaction.

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Key Concepts

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

Diazotization

Diazotization is a chemical reaction that involves converting an amine group (-NH2) into a diazonium salt (-N2+). This is typically achieved by treating the amine with sodium nitrite (NaNO2) in the presence of a strong acid like hydrochloric acid (HCl). The resulting diazonium salt is a key intermediate in various organic reactions, allowing for further substitution reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of diazonium salts, the nitrogen gas (N2) leaves, and a nucleophile, such as bromide ion (Br-) from CuBr, can replace it, leading to the formation of a new compound. This reaction is crucial for introducing different functional groups into aromatic systems.

Aromatic Compounds

Aromatic compounds are a class of cyclic compounds characterized by their stable ring structure and delocalized π-electrons, which follow Huckel's rule (4n + 2 π electrons). The presence of substituents, such as -NH2 and -NO2, can influence the reactivity and stability of these compounds. Understanding the electronic effects of these substituents is essential for predicting the outcomes of reactions involving aromatic systems.

Predict the products of the following reactions: (c)