When certain aromatic compounds are treated with formaldehyde, \(\mathrm{CH}_{2} \mathrm{O}\), and \(\mathrm{HCl}\), the \(\mathrm{CH}_{2} \mathrm{Cl}\) group is introduced onto the ring. This reaction is known as chloromethylation.

Short Answer

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Q: Explain the chloromethylation reaction when certain aromatic compounds react with formaldehyde and HCl. A: The chloromethylation reaction involves an aromatic compound reacting with formaldehyde and HCl, and proceeds through the following steps: 1. Formation of the chloromethyl cation by the reaction of formaldehyde and HCl. 2. Electrophilic aromatic substitution reaction where the aromatic compound attacks the electrophilic carbon in the chloromethyl cation, adding a CH2Cl group to the ring. 3. Restoring the aromaticity of the ring by a neighboring chloride ion abstracting a proton from the newly formed carbon attached to the ring. The final product is the aromatic compound with a CH2Cl group attached.

Step by step solution

01

Understand the reactants and products

Start by getting familiar with the reactants and products in this reaction. The reaction involves an aromatic compound, formaldehyde (\(\mathrm{CH}_{2}\mathrm{O}\)), and hydrochloric acid (\(\mathrm{HCl}\)). The product of the reaction is the aromatic compound with a \(\mathrm{CH}_{2}\mathrm{Cl}\) group attached to the ring.
02

Formation of chloromethyl cation

The first step in the reaction mechanism is the formation of a highly reactive species known as the chloromethyl cation (\(\mathrm{CH}_{2}\mathrm{Cl}^+\)) from formaldehyde and HCl. The HCl protonates the carbonyl oxygen in the formaldehyde, making it a better leaving group. A chloride ion then attacks the carbon atom, replacing the hydroxide group and forming the chloromethyl cation.
03

Electrophilic aromatic substitution reaction

The next step involves an electrophilic aromatic substitution reaction. The aromatic compound acts as a nucleophile and attacks the electrophilic carbon in the chloromethyl cation, temporarily losing its aromaticity. This results in the addition of a \(\mathrm{CH}_{2}\mathrm{Cl}\) group to the aromatic ring.
04

Restoring aromaticity

In order to regain its aromaticity, a proton from the newly formed carbon attached to the ring is abstracted by a neighboring chloride ion (a base). This process restores the aromaticity of the ring and completes the chloromethylation reaction.
05

Identify the final product

The final product of this reaction is the initial aromatic compound with a \(\mathrm{CH}_{2}\mathrm{Cl}\) group attached to the ring. This product is the result of the electrophilic aromatic substitution reaction involving the chloromethyl cation reacting with the aromatic ring, followed by the abstraction of a proton to restore aromaticity.

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