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Q62.

Expert-verified
Organic Chemistry
Found in: Page 453

Short Answer

Question: Why is compound X formed in the following reaction instead of its constitutional isomer Y?

Answer

The given reaction proceeds by the following mechanism:

Formation of the carbocation intermediate [1]

Carbocation intermediate [2]

Formation of the product X

The product Y is not formed because the carbocation intermediate [2] is not formed during the reaction.

See the step by step solution

Step by Step Solution

Step-by-Step SolutionStep 1: Constitutional isomers

The isomers, which differ from each other only in terms of structure but have the same molecular formula, are called constitutional isomers. These isomers differ from each other only in terms of the connectivity of atoms.

The constitutional isomers are further divided into three different categories: functional isomers, skeletal isomers, and positional isomers.

Step 2: Mechanism of the given reaction

For the given reaction, in the first step, there is the formation of a resonance-stabilized carbocation. This carbocation is formed by the reaction of the given compound with TsOH, as shown below.

Formation of the carbocation intermediate [1]

The above carbocation intermediate is formed because it is resonance-stabilized, and the positive charge is delocalized by the oxygen atom.

The following carbocation is not formed.

Carbocation intermediate [2]

This carbocation is not formed because this is not resonance-stabilized.

In the next step of the reaction, the nucleophilic attack on the carbocation intermediate takes place by the ethanol molecule. This results in the formation of product X, as shown below.

Formation of product X

Product Y is not formed because the carbocation intermediate [2] is not formed during the reaction.

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