Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

11. Radical Reactions

Anti Markovnikov Addition of Br

Organic Chemistry

11. Radical Reactions

Anti Markovnikov Addition of Br

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6:10 minutes

Problem 39d

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.
d.

Verified step by step guidance

Step 1: Analyze the reaction conditions. The presence of peroxide indicates that the reaction will follow the anti-Markovnikov addition mechanism. This means the bromine atom will add to the less substituted carbon of the double bond.

Step 2: Identify the structure of the starting alkene. The molecule contains two double bonds, one in the terminal position and one internal. Since HBr is in excess, both double bonds will react sequentially.

Step 3: For the first addition of HBr, the bromine will add to the less substituted carbon of the terminal double bond, following the anti-Markovnikov rule. This forms a primary alkyl bromide intermediate.

Step 4: For the second addition of HBr, the bromine will add to the less substituted carbon of the internal double bond, again following the anti-Markovnikov rule. This forms the final product.

Step 5: The final product will be the alkyl halide where bromine atoms are added to the less substituted carbons of both double bonds. Ignore stereoisomers as specified in the problem.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Anti-Markovnikov Addition

Anti-Markovnikov addition refers to the regioselectivity observed in the addition of HX (like HBr) to alkenes in the presence of peroxides. In this reaction, the hydrogen atom from HBr adds to the less substituted carbon of the alkene, resulting in the formation of the less stable, but more substituted alkyl halide. This contrasts with Markovnikov's rule, where the hydrogen would add to the more substituted carbon.

Alkyl Halides

Alkyl halides are organic compounds derived from alkanes that contain one or more halogen atoms (F, Cl, Br, I) replacing hydrogen atoms. They are classified based on the carbon atom to which the halogen is attached, such as primary, secondary, or tertiary alkyl halides. The structure and substitution pattern of alkyl halides significantly influence their reactivity and the types of reactions they undergo.

Reaction Mechanism

Understanding the reaction mechanism is crucial for predicting the products of chemical reactions. In the case of the anti-Markovnikov addition of HBr with peroxides, the mechanism involves the formation of free radicals, which leads to the addition of HBr across the double bond. This mechanism is distinct from ionic mechanisms and highlights the role of radical intermediates in determining the final product distribution.

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