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Predict the product(s) of the following reaction. Provide a complete mechanism showing the synthesis of the major product. Cl₂ hv

Predict the product(s) of the following reaction. Provide a complete mechanism showing the synthesis of the major product. Cl₂ hv

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Predict the product(s) of the following reaction. Provide a complete mechanism showing the synthesis of the major product.** ### Reaction: - **Starting Material:** Isopropylbenzene (cumene), represented by a benzene ring (hexagon with 3 alternating double bonds) attached to a chain with two methyl groups branching off the second carbon. - **Reagents:** - **Cl₂ (Chlorine gas)** - **hv (light)** indicating that the reaction occurs under photochemical conditions. ### Explanation: The reaction depicted involves the chlorination of isopropylbenzene under ultraviolet light, leading to a free radical halogenation reaction. This type of reaction follows the mechanism of free radical substitution, which involves three main steps: initiation, propagation, and termination. #### Mechanism Details: 1. **Initiation:** - The chlorine molecule (Cl₂) absorbs light energy (hv), leading to homolytic cleavage and the formation of two chlorine radicals (Cl•). 2. **Propagation:** - The chlorine radical abstracts a hydrogen atom from the benzylic position of isopropylbenzene, creating a benzylic radical. - The benzylic radical then reacts with another Cl₂ molecule to form the chlorinated product and regenerates a chlorine radical. 3. **Termination:** - Various termination steps could occur where two radicals combine, but these are less relevant to the product formation unless specified. The major product will be the benzylic chloride, where Cl substitutes for a hydrogen atom on the benzylic carbon due to the stability provided by resonance with the benzene ring.
Transcribed Image Text:**Predict the product(s) of the following reaction. Provide a complete mechanism showing the synthesis of the major product.** ### Reaction: - **Starting Material:** Isopropylbenzene (cumene), represented by a benzene ring (hexagon with 3 alternating double bonds) attached to a chain with two methyl groups branching off the second carbon. - **Reagents:** - **Cl₂ (Chlorine gas)** - **hv (light)** indicating that the reaction occurs under photochemical conditions. ### Explanation: The reaction depicted involves the chlorination of isopropylbenzene under ultraviolet light, leading to a free radical halogenation reaction. This type of reaction follows the mechanism of free radical substitution, which involves three main steps: initiation, propagation, and termination. #### Mechanism Details: 1. **Initiation:** - The chlorine molecule (Cl₂) absorbs light energy (hv), leading to homolytic cleavage and the formation of two chlorine radicals (Cl•). 2. **Propagation:** - The chlorine radical abstracts a hydrogen atom from the benzylic position of isopropylbenzene, creating a benzylic radical. - The benzylic radical then reacts with another Cl₂ molecule to form the chlorinated product and regenerates a chlorine radical. 3. **Termination:** - Various termination steps could occur where two radicals combine, but these are less relevant to the product formation unless specified. The major product will be the benzylic chloride, where Cl substitutes for a hydrogen atom on the benzylic carbon due to the stability provided by resonance with the benzene ring.
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