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

Nucleophilic Aromatic Substitution

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Nucleophilic Aromatic Substitution

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Multiple Choice

Which of the following compounds is most likely to undergo nucleophilic aromatic substitution via the addition-elimination pathway?

Molecule with a bromine atom and a methoxy group on a benzene ring.

Benzene ring with a bromine atom and a methoxy group in a different position.

Benzene ring with a bromine atom and a methyl group attached.

Benzene ring with two substituents: a bromine atom and a methoxy group.

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Verified step by step guidance

Identify the functional groups present in each compound. The compounds shown are aromatic rings with a bromine substituent and various other substituents such as carbonyl groups, methyl groups, and methoxy groups.

Understand the mechanism of nucleophilic aromatic substitution via the addition-elimination pathway. This mechanism typically involves the addition of a nucleophile to the aromatic ring, followed by the elimination of a leaving group.

Recognize that electron-withdrawing groups on the aromatic ring can stabilize the negative charge formed during the addition step, making the substitution more favorable. Common electron-withdrawing groups include nitro groups, carbonyl groups, and cyano groups.

Analyze the position of the substituents relative to the bromine atom. Ortho and para positions relative to the leaving group (bromine) are more favorable for nucleophilic aromatic substitution due to resonance stabilization.

Evaluate the compounds: The first compound has a carbonyl group ortho to the bromine, which is an electron-withdrawing group that can stabilize the intermediate formed during the addition step. This makes it more likely to undergo nucleophilic aromatic substitution via the addition-elimination pathway compared to the other compounds.