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

EAS:Synergistic and Competitive Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Synergistic and Competitive Groups

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3:56 minutes

Problem 58c,d

Textbook Question

For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO₃/H₂SO₄:
c.
d.

Verified step by step guidance

Step 1: Analyze the substituents on the benzene ring for compound c. The substituents are -OCH3 (methoxy group) and -Cl (chlorine). The methoxy group is an electron-donating group (activating, ortho/para-directing), while chlorine is an electron-withdrawing group (deactivating, ortho/para-directing). The methoxy group will dominate the directing effects due to its stronger activation.

Step 2: Predict the nitration sites for compound c. The methoxy group directs nitration to the ortho and para positions relative to itself. The chlorine group also directs nitration to its ortho and para positions, but its effect is weaker. Therefore, the nitration will primarily occur at the ortho and para positions relative to the methoxy group.

Step 3: Analyze the substituents on the benzene ring for compound d. The substituents are -OH (hydroxy group) and -COOH (carboxylic acid group). The hydroxy group is an electron-donating group (activating, ortho/para-directing), while the carboxylic acid group is an electron-withdrawing group (deactivating, meta-directing). The hydroxy group will dominate the directing effects due to its stronger activation.

Step 4: Predict the nitration sites for compound d. The hydroxy group directs nitration to the ortho and para positions relative to itself. The carboxylic acid group directs nitration to the meta position relative to itself, but its effect is weaker. Therefore, the nitration will primarily occur at the ortho and para positions relative to the hydroxy group.

Step 5: Summarize the nitration sites. For compound c, nitration occurs at the ortho and para positions relative to the methoxy group. For compound d, nitration occurs at the ortho and para positions relative to the hydroxy group.

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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. This process is crucial for understanding how compounds react with nitrating agents like HNO3 in the presence of H2SO4, which generates the nitronium ion (NO2+), the active electrophile in nitration.

Aromaticity

Aromaticity refers to the special stability and reactivity of certain cyclic compounds that follow Huckel's rule, which states that a compound must have (4n + 2) π electrons to be considered aromatic. This property influences the positions on the ring that are susceptible to electrophilic attack, making it essential to identify which carbons can be nitrated.

Regioselectivity in Nitration

Regioselectivity in nitration describes the preference of the electrophile to attack specific positions on the aromatic ring, influenced by substituents already present. Electron-donating groups activate the ring and direct substitution to ortho and para positions, while electron-withdrawing groups direct it to the meta position, which is critical for predicting the outcome of the nitration reaction.

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