Predict the products of the following reactions: (c) <
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Verified step by step guidance

1. Identify the starting material as an aromatic amine, specifically 2-nitroaniline, which has an amino group (NH2) and a nitro group (NO2) on a benzene ring.
2. Recognize that the reaction involves diazotization followed by a Sandmeyer reaction. The first step uses NaNO2 and HCl to convert the amino group into a diazonium salt.
3. Understand that the diazonium salt is unstable and can be replaced by a halogen using a copper(I) halide, in this case, CuBr, to form an aryl bromide.
4. Predict that the amino group (NH2) will be replaced by a bromine atom (Br) on the benzene ring, resulting in 2-nitrobromobenzene.
5. Consider the position of the nitro group, which remains unchanged, ensuring the product is correctly identified as 2-nitrobromobenzene.

Key Concepts

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 transformations such as substitution reactions.

Nucleophilic Aromatic Substitution

Nucleophilic aromatic substitution (NAS) is a reaction where a nucleophile replaces a leaving group on an aromatic ring. In this context, the diazonium salt generated from the amine can undergo substitution with a nucleophile, such as bromide ions (Br-) from CuBr. This reaction is facilitated by the electron-withdrawing nitro group, which stabilizes the negative charge developed during the reaction.

Reactivity of Diazonium Salts

Diazonium salts are highly reactive intermediates in organic chemistry, particularly in electrophilic aromatic substitution reactions. They can easily undergo substitution with various nucleophiles, including halides, phenols, and other aromatic compounds. The stability of the diazonium salt and the nature of the substituents on the aromatic ring significantly influence the reaction pathway and the products formed.