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

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

Previous problemNext problem

3:13 minutes

Problem 60

Textbook Question

δ-Hydroxyaldehydes are in equilibrium with their hemiacetal form. Predict the product that would form upon treatment of the hemiacetal with Dess–Martin periodinane.

Verified step by step guidance

Understand the structure of δ-Hydroxyaldehydes and hemiacetals. A δ-Hydroxyaldehyde contains both an aldehyde group and a hydroxyl group, which can form a cyclic hemiacetal through intramolecular reaction.

Recognize the role of Dess–Martin periodinane (DMP) in organic reactions. DMP is a mild oxidizing agent commonly used to oxidize alcohols to carbonyl compounds.

Identify the functional groups present in the hemiacetal. The hemiacetal contains an alcohol group and an ether linkage formed from the aldehyde and hydroxyl group.

Predict the reaction outcome when the hemiacetal is treated with Dess–Martin periodinane. DMP will oxidize the alcohol group in the hemiacetal to a carbonyl group, typically forming an aldehyde or ketone.

Consider the structural changes. The oxidation of the alcohol group in the hemiacetal will lead to the formation of a new carbonyl group, resulting in a more stable cyclic structure, likely a lactone if the original δ-Hydroxyaldehyde was cyclic.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Hemiacetal Formation

Hemiacetals are formed when an aldehyde reacts with an alcohol, resulting in a molecule with both an alcohol and an ether functional group on the same carbon. This equilibrium is crucial in understanding the behavior of δ-hydroxyaldehydes, as they can readily convert to hemiacetals under certain conditions.

Dess–Martin Periodinane

Dess–Martin periodinane is a mild oxidizing agent used in organic chemistry to selectively oxidize alcohols to aldehydes or ketones. It is particularly useful for oxidizing primary alcohols to aldehydes without over-oxidation to carboxylic acids, making it ideal for transforming hemiacetals into their corresponding aldehydes.

Oxidation of Alcohols

Oxidation of alcohols involves the conversion of an alcohol group into a carbonyl group, either an aldehyde or a ketone. In the context of hemiacetals, the alcohol portion can be oxidized to form an aldehyde, which is the expected product when treated with Dess–Martin periodinane, highlighting the transformation of functional groups in organic reactions.

Watch next

Master Reagents with a bite sized video explanation from Johnny

Start learning