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What is the expected major product of the following reaction? HBr ROOR Br Br Br Br Br II %3D IV

What is the expected major product of the following reaction? HBr ROOR Br Br Br Br Br II %3D IV

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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**Organic Chemistry Reaction Mechanism: Predicting the Major Product** **Question:** What is the expected major product of the following reaction? **Reactants and Conditions:** A five-membered cyclopentene ring (cyclopentane with one double bond) reacts with Hydrogen Bromide (HBr) in the presence of a peroxide initiator (ROOR). **Possible Products:** 1. Cyclopentane with a Bromine atom (Br) attached to the carbon that was part of the double bond. 2. Cyclopentane with a Methyl group (CH₃) attached to the carbon that was part of the double bond. 3. Cyclopentane with a Bromine atom attached to the carbon adjacent to the double bond. 4. Cyclopentane with a Bromine atom attached to the other carbon adjacent to the double bond. 5. Cyclopentane with two Bromine atoms, one on each carbon previously involved in the double bond. **Answer Choices:** - (A) I - (B) II - (C) III - (D) IV - (E) V **Explanation:** The addition of HBr to an alkene (in this case cyclopentene) proceeds via a free-radical mechanism in the presence of peroxides (ROOR). This reaction often follows the anti-Markovnikov rule due to the formation of the more stable radical intermediate. The product can be predicted based on this rule, where the Bromine attaches to the carbon that is not part of the double bond (the carbon that does not participate in forming the more stable radical). Based on this, the answer choice considering both electron and structural stability is likely: - (A) I However, to be certain of the product, a detailed understanding of both the reaction conditions and the mechanistic pathway is required. The radical initiator promotes the anti-Markovnikov addition, resulting in a product where the Bromine atom attaches to the less substituted carbon of the double bond. Hence, the structure in choice (I) should be the major product.
Transcribed Image Text:**Organic Chemistry Reaction Mechanism: Predicting the Major Product** **Question:** What is the expected major product of the following reaction? **Reactants and Conditions:** A five-membered cyclopentene ring (cyclopentane with one double bond) reacts with Hydrogen Bromide (HBr) in the presence of a peroxide initiator (ROOR). **Possible Products:** 1. Cyclopentane with a Bromine atom (Br) attached to the carbon that was part of the double bond. 2. Cyclopentane with a Methyl group (CH₃) attached to the carbon that was part of the double bond. 3. Cyclopentane with a Bromine atom attached to the carbon adjacent to the double bond. 4. Cyclopentane with a Bromine atom attached to the other carbon adjacent to the double bond. 5. Cyclopentane with two Bromine atoms, one on each carbon previously involved in the double bond. **Answer Choices:** - (A) I - (B) II - (C) III - (D) IV - (E) V **Explanation:** The addition of HBr to an alkene (in this case cyclopentene) proceeds via a free-radical mechanism in the presence of peroxides (ROOR). This reaction often follows the anti-Markovnikov rule due to the formation of the more stable radical intermediate. The product can be predicted based on this rule, where the Bromine attaches to the carbon that is not part of the double bond (the carbon that does not participate in forming the more stable radical). Based on this, the answer choice considering both electron and structural stability is likely: - (A) I However, to be certain of the product, a detailed understanding of both the reaction conditions and the mechanistic pathway is required. The radical initiator promotes the anti-Markovnikov addition, resulting in a product where the Bromine atom attaches to the less substituted carbon of the double bond. Hence, the structure in choice (I) should be the major product.
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