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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Tautomerization

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Tautomerization

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Multiple Choice

Draw the enol tautomer for cyclopentanone

Enol tautomer of cyclopentanone with hydroxyl group at the alpha-carbon.

Enol tautomer of cyclopentanone with a double bond at the alpha-carbon.

Enol tautomer of cyclopentanone showing hydroxyl group and double bond.

Enol tautomer of cyclopentanone with hydroxyl group and double bond at the alpha-carbon.

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Verified step by step guidance

Identify the structure of cyclopentanone, which is a five-membered ring with a ketone group (C=O) attached to one of the carbons.

Understand that tautomerization involves the migration of a hydrogen atom and the shift of a double bond. In keto-enol tautomerism, the keto form (C=O) is converted to the enol form (C=C-OH).

Locate the alpha hydrogen in cyclopentanone, which is the hydrogen atom on the carbon adjacent to the carbonyl carbon.

Move the alpha hydrogen to the oxygen of the carbonyl group, forming an OH group, and shift the double bond from the C=O to between the alpha carbon and the carbonyl carbon, forming a C=C double bond.

Draw the resulting enol tautomer, which will have an OH group attached to the carbon that was originally the carbonyl carbon, and a C=C double bond between the former carbonyl carbon and the alpha carbon.