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

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

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3:10 minutes

Problem 41c

Textbook Question

Predict the products formed when m-cresol (m-methylphenol) reacts with
(c) bromine in CCl₄ in the dark

Verified step by step guidance

Identify the structure of m-cresol (m-methylphenol). It consists of a benzene ring with a hydroxyl (-OH) group and a methyl (-CH₃) group in the meta position relative to each other.

Understand the reaction conditions: Bromine (Br₂) in CCl₄ (carbon tetrachloride) in the dark. This indicates that the reaction will proceed via electrophilic aromatic substitution, as there is no light or catalyst to promote a radical reaction.

Recognize the directing effects of the substituents on the benzene ring. The hydroxyl (-OH) group is an activating, ortho/para-directing group, while the methyl (-CH₃) group is also an activating, ortho/para-directing group. However, since the groups are in the meta position relative to each other, their directing effects will influence different positions on the ring.

Determine the positions on the benzene ring where bromine will substitute. The -OH group will direct bromine to the ortho and para positions relative to itself, while the -CH₃ group will direct bromine to the ortho and para positions relative to itself. The overlap of these directing effects will determine the most likely substitution sites.

Draw the possible products based on the substitution pattern. Consider steric hindrance and electronic effects to predict the major product(s). Ensure that the bromine atom is added to the position(s) that align with the combined directing effects of the -OH and -CH₃ groups.

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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 (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of m-cresol, the presence of the methyl group and the hydroxyl group influences the reactivity and orientation of the substitution, typically directing electrophiles to the ortho and para positions relative to the substituents.

Bromination of Aromatic Compounds

Bromination is a specific type of electrophilic aromatic substitution where bromine acts as the electrophile. In the presence of a non-polar solvent like CCl4, bromine can react with m-cresol to form brominated products. The reaction typically occurs at the positions on the aromatic ring that are most activated by the existing substituents.

Influence of Substituents on Reactivity

The reactivity of aromatic compounds in electrophilic substitution reactions is significantly influenced by the nature of substituents already present on the ring. In m-cresol, the hydroxyl group is a strong activating group that increases the electron density of the ring, while the methyl group is a weakly activating group. This combination affects the regioselectivity of the bromination, favoring substitution at the positions that are ortho or para to the hydroxyl group.

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