**Chlorination of Hydrocarbons: A Comparative Study of Molecules 4 and 5****Question:**Explain why the major product for the chlorination of molecule 4 is chlorination of the secondary carbon, but the chlorination of molecule 5 favors chlorination at the primary carbon.**Chemical Reactions and Product Distribution:**1. **Molecule 4:** - **Structure:** Cyclopropane ring - **Reaction:** Chlorination in the presence of light (\( \text{Cl}_2 \)) - **Products:** - Secondary chloride (66%) - Two other chlorinated compounds (21% and 13%) - **Product Distribution:** Major product is the secondary chloride with 66%.2. **Molecule 5:** - **Structure:** Isobutane - **Reaction:** Chlorination in the presence of light (\( \text{Cl}_2 \)) - **Products:** - Primary chloride (64%) - Secondary chloride (36%) - **Product Distribution:** Major product is the primary chloride with 64%.**Explanation:***The differences in chlorination outcomes for molecule 4 and molecule 5 can be attributed to their structural differences and the stability of the resulting radicals upon chlorination.*1. **Molecule 4 - Cyclopropane Structure:** - The secondary carbon is part of a strained three-membered ring. - The strain in the cyclopropane ring can stabilize the transition state of the radical intermediate formed after hydrogen abstraction from the secondary carbon, leading to a major product with chlorine on the secondary carbon.2. **Molecule 5 - Isobutane Structure:** - Isobutane is less strained compared to cyclopropane. - In isobutane, radical stability favors the formation of the primary radical due to steric considerations and hyperconjugation, which result in a more stabilized radical intermediate when chlorine is added to the primary carbon.Therefore, the intrinsic strain in molecule 4 and the consequent effects on radical stability and transition states lead to predominantly secondary chlorination, while in molecule 5, less structural strain allows for preferential primary chlorination due to less steric hindrance and stabilization factors.

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5) Explain why the major product for the chlorination of molecule 4 is chlorination of the secondary carbon, but the chlorination of molecule 5 favors chlorination at the primary carbon. CI Cl2 CI Cl2 CI .CI light light molecule 4 molecule 5 36% 64% 21% 13% 66% Explanation

5) Explain why the major product for the chlorination of molecule 4 is chlorination of the secondary carbon, but the chlorination of molecule 5 favors chlorination at the primary carbon. CI Cl2 CI Cl2 CI .CI light light molecule 4 molecule 5 36% 64% 21% 13% 66% Explanation

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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