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 and Reducing Agents

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Oxidizing and Reducing Agents

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3:17 minutes

Problem 53e

Textbook Question

The intermediates for the oxidation of isopropanol to acetone are shown. Calculate oxidation numbers for the indicated atoms, then use them to determine in which step oxidation occurs.
(e)

Verified step by step guidance

Identify the structure of isopropanol (C3H8O) and acetone (C3H6O). Note that isopropanol is a secondary alcohol, and acetone is a ketone.

Determine the oxidation number of the carbon atom in isopropanol that is bonded to the hydroxyl group (OH). In organic compounds, carbon typically has an oxidation number of -4, but this can vary based on its bonding.

Calculate the oxidation number of the same carbon atom in acetone. Remember that in a ketone, the carbonyl carbon is bonded to an oxygen atom, which is more electronegative.

Compare the oxidation numbers of the carbon atom in isopropanol and acetone. An increase in the oxidation number indicates oxidation.

Identify the step in the reaction mechanism where the oxidation number of the carbon atom increases, signifying the oxidation step in the conversion of isopropanol to acetone.

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Key Concepts

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

Oxidation Numbers

Oxidation numbers are a way of keeping track of electrons in atoms as they undergo chemical reactions. They are assigned to atoms based on a set of rules, such as the oxidation number of a free element being zero and the sum of oxidation numbers in a neutral compound being zero. Calculating oxidation numbers helps identify which atoms are oxidized or reduced in a reaction.

Oxidation and Reduction

Oxidation is the process where an atom loses electrons, resulting in an increase in its oxidation number, while reduction is the gain of electrons, leading to a decrease in oxidation number. In organic chemistry, oxidation often involves the addition of oxygen or the removal of hydrogen. Identifying oxidation and reduction steps is crucial for understanding reaction mechanisms.

Reaction Intermediates

Reaction intermediates are transient species that appear in the steps between reactants and products in a chemical reaction. They are often unstable and cannot be isolated under normal conditions. Understanding intermediates is essential for mapping out the reaction pathway and determining where oxidation or reduction occurs in multi-step processes.

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