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:Any Carbocation Mechanism

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Any Carbocation Mechanism

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4:53 minutes

Problem 18

Textbook Question

What are the products of the following reactions?b.

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Step 1: Identify the functional groups in the molecule. The given compound contains a carboxylic acid group (-COOH) attached to a benzyl group (benzene ring with a CH2 group).

Step 2: Recognize the reaction conditions. The presence of H+ (acidic conditions) suggests a decarboxylation reaction, which is common for carboxylic acids with a β-carbonyl group.

Step 3: Analyze the structure for decarboxylation. The carboxylic acid group is adjacent to a carbonyl group, making it suitable for decarboxylation under acidic conditions.

Step 4: Predict the mechanism. In acidic conditions, the carboxylic acid group will lose CO2 (carbon dioxide) via a cyclic transition state, leaving behind a ketone group.

Step 5: Determine the product. After decarboxylation, the benzyl group will remain attached to the ketone, resulting in phenylacetone (C6H5-CH2-CO-CH3).

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Key Concepts

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

Aromatic Compounds

Aromatic compounds are cyclic structures that follow Huckel's rule, containing a planar ring of atoms with delocalized pi electrons. This delocalization imparts unique stability and reactivity characteristics, making them prone to electrophilic substitution reactions. Understanding the structure and stability of aromatic compounds is crucial for predicting their behavior in chemical reactions.

Carbocation Formation

Carbocations are positively charged species that contain a carbon atom with only six electrons in its valence shell, making them electron-deficient and highly reactive. They often form during reactions involving the loss of a leaving group or protonation of an alkene. Recognizing the conditions under which carbocations form is essential for predicting the products of organic reactions.

Electrophilic Substitution Reactions

Electrophilic substitution reactions are a class of reactions where an electrophile replaces a hydrogen atom in an aromatic compound. This process typically involves the generation of a carbocation intermediate, followed by deprotonation to restore aromaticity. Understanding the mechanism of these reactions is vital for predicting the products formed when aromatic compounds react with electrophiles.

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