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

16. Conjugated Systems

Reactions at the Allylic Position

Organic Chemistry

16. Conjugated Systems

Reactions at the Allylic Position

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Multiple Choice

What are the substitution products of the following reaction?

substitution products

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Verified step by step guidance

Identify the type of reaction: The given reaction involves a bromocyclopentene compound reacting with ethanol (EtOH). This suggests a nucleophilic substitution reaction, likely an SN1 mechanism due to the presence of a secondary allylic bromide.

Consider the mechanism: In an SN1 reaction, the leaving group (Br) departs first, forming a carbocation intermediate. The allylic position stabilizes the carbocation through resonance, allowing for potential rearrangements.

Analyze the carbocation stability: The allylic carbocation can resonate, leading to two possible carbocation intermediates. This resonance stabilization is crucial for the reaction pathway.

Nucleophile attack: Ethanol (EtOH) acts as the nucleophile, attacking the carbocation. Due to the resonance, the nucleophile can attack at either of the two carbocation positions, leading to different substitution products.

Consider stereochemistry: Since the reaction proceeds through a planar carbocation intermediate, the nucleophile can attack from either side, leading to racemic mixtures if chiral centers are formed. The final products will be a mixture of regioisomers and potentially stereoisomers.