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Chapter 19: Problem 8

Write a mechanism for the hydrolysis of the following iminium chloride in aqueous HCl.

Short Answer

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Question: Describe the hydrolysis mechanism of an iminium chloride in aqueous HCl. Answer: The hydrolysis mechanism of an iminium chloride in aqueous HCl involves five main steps: 1) identifying the starting iminium chloride compound, 2) nucleophilic attack of water on the electrophilic carbon of the iminium cation, 3) a proton transfer to the chlorine atom, generating a hydroxyl group, 4) tautomerization to reform the C=N double bond, and 5) elimination of the chloride ion, resulting in the formation of amine and carbonyl compounds.

Step by step solution

01

Identify the starting compound

First, it's important to identify the iminium chloride that is going to be hydrolyzed in aqueous HCl. This will be the starting point for the hydrolysis mechanism.
02

Attack of water

In the initial step of hydrolysis, a water molecule acts as a nucleophile and attacks the electrophilic carbon of the iminium cation, resulting in the formation of a tetrahedral intermediate. The oxygen of the water molecule has a higher electron density that enables this nucleophilic attack.
03

Proton transfer

In the next step, one of the hydrogen atoms from the oxygen of the tetrahedral intermediate is transferred to the chlorine atom, which acts as a base. This proton transfer generates a hydroxyl group on the carbon atom and a chloride ion in the solution.
04

Tautomerization

Tautomerization is an important process that interconverts two isomers with the same molecular formula. In this case, a proton is transferred from the hydroxyl group to the nitrogen atom, generating a double bond between the carbon and oxygen atoms and Reforming the C=N double bond.
05

Formation of the final products

The final step of the hydrolysis mechanism is the elimination of the chloride ion. The double bond between the nitrogen and carbon atom breaks and migrates to the nitrogen atom, expelling the chloride ion. This produces the hydrolyzed products, namely the amine and carbonyl compounds. By following these steps, the hydrolysis mechanism of the iminium chloride in aqueous HCl can be effectively described.

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