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Determine the product(s) of the following substitution reaction: Cl2 hv

Determine the product(s) of the following substitution reaction: 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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### Determine the product(s) of the following substitution reaction: #### Reactants: - A cyclopentane ring with a single methyl group attached to one of the carbon atoms. - Chlorine gas (Cl₂) in the presence of light (hv). #### Explanation: The given reaction is a radical substitution reaction facilitated by ultraviolet (UV) light (hv). When chlorine gas (Cl₂) is exposed to UV light, it dissociates into two chlorine radicals (Cl·). These radicals then react with the hydrogen atoms on the cyclopentane ring, particularly targeting the position that can yield the most stable radical intermediate. In this reaction, chlorine can replace a hydrogen atom on the cyclopentane ring especially at the position where it would yield a secondary or tertiary carbon radical, which are more stable than primary carbon radicals. Given this, the possible products of the reaction are: 1. **Chloromethylcyclopentane**: The chlorine radical replaces a hydrogen atom on the methyl group. 2. **1-Chlorocyclopentane**: The chlorine radical replaces a hydrogen atom on one of the carbon atoms in the cyclopentane ring, leading to the formation of a secondary or tertiary carbon radical intermediate, which then stabilizes by forming 1-chlorocyclopentane. Visually, if we denote the carbon atoms in the ring and the methyl group, the substitutions would occur as follows: 1. **Replacing a hydrogen in the methyl group:** ``` Cl | /----C----\ | | | | \__________/ Cl replaces one hydrogen in the methyl group attached to the cyclopentane ring. ``` 2. **Replacing a hydrogen in the ring (at a secondary or tertiary position):** ``` Cl | / \ C C / \ / \ C C - C |_______| Cl replaces one hydrogen at a ring carbon position. The ring maintains its cyclopentane structure. ``` Hence, the products of this reaction will primarily be chloromethylcyclopentane and 1-chlorocyclopentane.
Transcribed Image Text:### Determine the product(s) of the following substitution reaction: #### Reactants: - A cyclopentane ring with a single methyl group attached to one of the carbon atoms. - Chlorine gas (Cl₂) in the presence of light (hv). #### Explanation: The given reaction is a radical substitution reaction facilitated by ultraviolet (UV) light (hv). When chlorine gas (Cl₂) is exposed to UV light, it dissociates into two chlorine radicals (Cl·). These radicals then react with the hydrogen atoms on the cyclopentane ring, particularly targeting the position that can yield the most stable radical intermediate. In this reaction, chlorine can replace a hydrogen atom on the cyclopentane ring especially at the position where it would yield a secondary or tertiary carbon radical, which are more stable than primary carbon radicals. Given this, the possible products of the reaction are: 1. **Chloromethylcyclopentane**: The chlorine radical replaces a hydrogen atom on the methyl group. 2. **1-Chlorocyclopentane**: The chlorine radical replaces a hydrogen atom on one of the carbon atoms in the cyclopentane ring, leading to the formation of a secondary or tertiary carbon radical intermediate, which then stabilizes by forming 1-chlorocyclopentane. Visually, if we denote the carbon atoms in the ring and the methyl group, the substitutions would occur as follows: 1. **Replacing a hydrogen in the methyl group:** ``` Cl | /----C----\ | | | | \__________/ Cl replaces one hydrogen in the methyl group attached to the cyclopentane ring. ``` 2. **Replacing a hydrogen in the ring (at a secondary or tertiary position):** ``` Cl | / \ C C / \ / \ C C - C |_______| Cl replaces one hydrogen at a ring carbon position. The ring maintains its cyclopentane structure. ``` Hence, the products of this reaction will primarily be chloromethylcyclopentane and 1-chlorocyclopentane.
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