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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4:41 minutes

Problem 39c

Textbook Question

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

Verified step by step guidance

Step 1: Recognize the reaction type. The presence of peroxide indicates that this is a free radical addition of HBr to an alkene, following the anti-Markovnikov rule. This means the bromine atom will add to the less substituted carbon of the double bond.

Step 2: Identify the structure of the alkene. The given alkene is 2-methyl-2-butene, which has a double bond between the second and third carbons.

Step 3: Determine the less substituted carbon in the double bond. In 2-methyl-2-butene, the less substituted carbon is the third carbon, as the second carbon is bonded to three other carbons.

Step 4: Predict the product. The bromine atom will add to the third carbon, and the hydrogen atom will add to the second carbon, resulting in the formation of 3-bromo-2-methylbutane.

Step 5: Confirm the major product. Since the reaction follows the anti-Markovnikov rule and stereoisomers are ignored, the major product will be 3-bromo-2-methylbutane.

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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 addition of HX (where X is a halogen) to alkenes in a manner that results in the halogen attaching to the less substituted carbon atom. This is typically facilitated by the presence of peroxides, which promote a radical mechanism, leading to the formation of the less stable radical intermediate and ultimately favoring the less substituted product.

Radical Mechanism

A radical mechanism involves the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of alkene reactions with HBr in the presence of peroxides, the radical mechanism allows for the anti-Markovnikov addition by generating bromine radicals that add to the alkene, leading to the formation of the product with the bromine on the less 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. The structure and substitution pattern of the alkyl halide influence its reactivity and stability, which is crucial when determining the yield of products in reactions involving alkenes and halogen acids, especially under radical conditions.

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