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

Previous problemNext problem

7: minutes

Problem 44

Textbook Question

Predict the site(s) of electrophilic attack on these compounds.

Verified step by step guidance

Step 1: Analyze the substituents on the aromatic ring for compound (a). The hydroxyl group (-OH) is an electron-donating group through resonance and inductive effects, activating the ring towards electrophilic attack. The nitro group (-NO₂) is an electron-withdrawing group through resonance and inductive effects, deactivating the ring and directing electrophilic attack to meta positions relative to itself.

Step 2: Determine the directing effects for compound (a). The -OH group is an ortho/para-directing group, while the -NO₂ group is a meta-directing group. The competition between these groups will influence the site of electrophilic attack.

Step 3: For compound (a), predict the most likely sites of electrophilic attack. The -OH group will activate the ortho and para positions relative to itself, but the para position is less sterically hindered. The -NO₂ group will deactivate the ortho and para positions relative to itself, favoring meta positions.

Step 4: Analyze the substituents on the aromatic ring for compound (b). The methoxy group (-OCH₃) is an electron-donating group through resonance and inductive effects, activating the ring towards electrophilic attack. The methyl group (-CH₃) is also an electron-donating group, but its effect is weaker compared to -OCH₃.

Step 5: Determine the directing effects for compound (b). Both -OCH₃ and -CH₃ are ortho/para-directing groups. The -OCH₃ group will strongly activate the ortho and para positions relative to itself, while the -CH₃ group will activate its own ortho and para positions. The most likely sites of electrophilic attack will be the positions that are activated by both groups or are sterically favorable.

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 (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The aromatic system's stability allows it to react with electrophiles, leading to the formation of new substituents. Understanding EAS is crucial for predicting where electrophiles will attack on substituted aromatic compounds.

Activating and Deactivating Groups

Substituents on an aromatic ring can either activate or deactivate the ring towards electrophilic attack. Activating groups, such as -OH and -OCH3, increase the electron density of the ring, making it more reactive. In contrast, deactivating groups, like -NO2, withdraw electron density, making the ring less reactive. Recognizing these effects is essential for predicting the site of electrophilic attack.

Ortho/Para vs. Meta Directing Effects

The position of electrophilic attack on an aromatic compound is influenced by the nature of the substituents. Activating groups typically direct electrophiles to the ortho and para positions, while deactivating groups direct them to the meta position. This distinction is vital for understanding the regioselectivity of electrophilic aromatic substitution reactions and predicting the products formed.

Watch next

Master Activity and Directing Effects with a bite sized video explanation from Johnny

Start learning