Predict the product(s) of the reactions shown.
(b)

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Identify the starting material: The compound is an aromatic amine, specifically an aniline derivative with a tert-butyl group attached to the benzene ring.

Understand the reaction conditions: The first step involves NaNO2 and HCl, which is used to convert the amine group into a diazonium salt. This is known as diazotization.

Write the diazotization reaction: The amine group (NH2) will be transformed into a diazonium group (N2+), forming an aryl diazonium salt. The reaction can be represented as: NH2 + NaNO2 + HCl → N2+ + Cl- + H2O.

Consider the second step: The diazonium salt reacts with CuCl, which is a Sandmeyer reaction. This reaction replaces the diazonium group with a chlorine atom.

Predict the final product: The tert-butyl group remains unchanged, and the diazonium group is replaced by a chlorine atom, resulting in a chlorinated aromatic compound.

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Key Concepts

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

Diazotization Reaction

Diazotization is a chemical reaction that converts an aromatic amine into a diazonium salt using nitrous acid, typically generated in situ from sodium nitrite and hydrochloric acid. This reaction is crucial for introducing a diazonium group, which can be further transformed into various functional groups through substitution reactions.

Sandmeyer Reaction

The Sandmeyer reaction involves the substitution of an aromatic diazonium group with a halide or pseudohalide using copper(I) salts. In this case, CuCl facilitates the replacement of the diazonium group with a chlorine atom, allowing for the synthesis of aryl chlorides from aryl amines, expanding the functional diversity of aromatic compounds.

Aromatic Substitution

Aromatic substitution refers to the replacement of a substituent on an aromatic ring with another group. In the context of the reaction shown, the diazonium group formed from the amine is substituted by a chlorine atom, demonstrating the versatility of aromatic compounds in undergoing various substitution reactions to yield different products.

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