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

Previous problemNext problem

3:59 minutes

Problem 45c

Textbook Question

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

Verified step by step guidance

Identify the type of bromination reaction: In organic chemistry, bromination typically involves the addition of bromine (Br₂) to a compound. The reaction can be either radical bromination or electrophilic addition, depending on the substrate.

Determine the substrate structure: Analyze the given substrate to understand its structure. Is it an alkane, alkene, or aromatic compound? This will influence the mechanism of bromination.

Select the appropriate mechanism: For alkanes, radical bromination is common, where a bromine radical abstracts a hydrogen atom. For alkenes, electrophilic addition occurs, where the π bond attacks a bromine molecule, forming a bromonium ion intermediate.

Consider regioselectivity and stereochemistry: In radical bromination, the most stable radical intermediate will form, often leading to the most substituted alkyl bromide. In electrophilic addition, Markovnikov's rule applies, where the bromine adds to the more substituted carbon.

Predict the major product: Based on the mechanism and regioselectivity, predict the structure of the major product. Ensure to consider any possible rearrangements or stereochemical outcomes if applicable.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution (EAS) is a reaction mechanism where an aromatic ring, such as benzene, undergoes substitution by an electrophile. In bromination, the aromatic ring reacts with bromine in the presence of a catalyst like FeBr3, facilitating the formation of a bromonium ion that substitutes a hydrogen atom on the ring, maintaining aromaticity.

Regioselectivity in Aromatic Substitution

Regioselectivity refers to the preference of a chemical reaction to yield a particular structural isomer when multiple possibilities exist. In bromination of substituted aromatic rings, the position of the substituents influences the site of electrophilic attack, often favoring ortho and para positions due to resonance and steric effects, especially if the substituent is an electron-donating group.

Activating and Deactivating Groups

Substituents on an aromatic ring can be classified as activating or deactivating based on their ability to donate or withdraw electrons. Activating groups, like -OH or -NH2, increase the ring's reactivity towards electrophiles and direct substitution to ortho/para positions. Deactivating groups, such as -NO2, withdraw electrons, making the ring less reactive and often directing substitution to the meta position.

Watch next

Master The one reaction that alkanes will actually undergo. with a bite sized video explanation from Johnny

Start learning