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

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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7:28 minutes

Problem 6f

Textbook Question

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.
(f) 1-methylcyclohexanol → 2-methylcyclohexanone (several steps)

Verified step by step guidance

Step 1: Recognize the transformation. The problem involves converting 1-methylcyclohexanol (a secondary alcohol) into 2-methylcyclohexanone (a ketone). This requires oxidation and a shift of the methyl group from position 1 to position 2.

Step 2: Plan the oxidation step. To oxidize the secondary alcohol to a ketone, you can use a chromium-based reagent such as pyridinium chlorochromate (PCC) or Jones reagent (CrO₃ in H₂SO₄). Alternatively, for a chromium-free option, you can use Dess-Martin periodinane (DMP) or Swern oxidation.

Step 3: Consider the methyl group migration. After oxidation, you need to shift the methyl group from position 1 to position 2. This can be achieved through a rearrangement reaction, such as a pinacol rearrangement, which involves acidic conditions to promote the migration.

Step 4: Suggest the chromium-based method. Use PCC or Jones reagent to oxidize 1-methylcyclohexanol to 1-methylcyclohexanone. Then, treat the ketone with an acid catalyst (e.g., H₂SO₄) to induce the methyl group migration, forming 2-methylcyclohexanone.

Step 5: Suggest the chromium-free method. Use Dess-Martin periodinane (DMP) or Swern oxidation to oxidize 1-methylcyclohexanol to 1-methylcyclohexanone. Follow this with the same acid-catalyzed rearrangement to achieve the desired product, 2-methylcyclohexanone.

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Key Concepts

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

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, these reactions are crucial for converting alcohols into carbonyl compounds, such as ketones. Understanding the mechanisms of oxidation helps in selecting appropriate reagents for synthesizing compounds like 2-methylcyclohexanone from 1-methylcyclohexanol.

Chromium Reagents

Chromium reagents, such as chromium trioxide (CrO3) or pyridinium chlorochromate (PCC), are commonly used in organic synthesis for the oxidation of alcohols to carbonyl compounds. These reagents are effective but can be toxic and environmentally hazardous, necessitating careful handling and disposal. Knowledge of their reactivity and selectivity is essential for proposing suitable methods in laboratory syntheses.

Alternative Oxidation Methods

Chromium-free oxidation methods, such as using Dess-Martin periodinane or Swern oxidation, provide safer and more environmentally friendly alternatives for converting alcohols to ketones. These methods often have milder reaction conditions and fewer toxic byproducts, making them attractive options in organic synthesis. Familiarity with these alternatives is important for suggesting diverse synthetic pathways.

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Related Practice

Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(e)

(f)

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(d)

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(f)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(k)

(l)

Textbook Question

Show how you would make each compound, beginning with an alcohol of your choice.

(g)

(h)

Textbook Question

Compounds containing deuterium (D = ²H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD₄, equivalent in reactivity to LiAlH₄. Show how to make these deuterium-labeled compounds, using LiAlD₄ and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

Textbook Question

Both NaBH₄ and NaBD₄ are commercially available, and D₂O is common and inexpensive. Show how you would synthesize the following labeled compounds, starting with butan-2-one.

(a)

Textbook Question

Suggest the most appropriate reagent for each synthesis, and explain your choice.

(c)

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