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

Free Radical Halogenation

Organic Chemistry

11. Radical Reactions

Free Radical Halogenation

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2:20 minutes

Problem 45b

Textbook Question

Predict the major product of the following bromination reactions.
(b)

Verified step by step guidance

Identify the type of bromination reaction: Bromination can occur through radical substitution or electrophilic addition, depending on the substrate. For alkanes, radical bromination is common, while for alkenes, electrophilic addition is typical.

Determine the substrate structure: Analyze the given substrate to identify if it is an alkane, alkene, or another type of organic molecule. This will guide the mechanism of bromination.

Consider regioselectivity and stereoselectivity: In radical bromination, the most stable radical intermediate is favored, often leading to bromination at the most substituted carbon. In electrophilic addition to alkenes, Markovnikov's rule applies, where the bromine adds to the more substituted carbon.

Draw the mechanism: For radical bromination, initiate with the formation of bromine radicals, followed by propagation steps where the radical abstracts a hydrogen and bromine adds to the carbon. For electrophilic addition, show the formation of a carbocation intermediate and subsequent bromine addition.

Predict the major product: Based on the mechanism and the stability of intermediates, predict the structure of the major product. Consider any possible rearrangements or side reactions that might influence the outcome.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution is a reaction where an electrophile replaces a hydrogen atom in an aromatic ring. In bromination, bromine acts as the electrophile, facilitated by a catalyst like FeBr3, which helps generate the active bromine species. Understanding this mechanism is crucial for predicting the position and nature of the substitution on the aromatic ring.

Regioselectivity in Aromatic Substitution

Regioselectivity refers to the preference for a chemical reaction to occur at one location over others in a molecule. In aromatic bromination, the position of substitution is influenced by existing substituents on the ring, which can be activating or deactivating and ortho/para or meta-directing. Identifying these effects helps predict the major product's structure.

Activating and Deactivating Groups

Activating groups increase the reactivity of the aromatic ring towards electrophilic substitution, often directing the electrophile to ortho and para positions. Deactivating groups reduce reactivity and typically direct substitution to the meta position. Recognizing these groups in the substrate is essential for determining the major product in bromination reactions.