Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question
**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.
expand button
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.
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY