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

22. Carboxylic Acid Derivatives: NAS

Carboxylation

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylation

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1:17 minutes

Problem 11d

Textbook Question

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(d) butan-2-ol → 2-methylbutanoic acid

Verified step by step guidance

Step 1: Begin by oxidizing butan-2-ol to form the corresponding ketone, butan-2-one. This can be achieved using an oxidizing agent such as PCC (Pyridinium Chlorochromate) or Jones reagent. The reaction involves the removal of two hydrogen atoms from the alcohol group.

Step 2: Perform a nucleophilic addition reaction to introduce a methyl group at the alpha-carbon of butan-2-one. This can be done using a Grignard reagent (e.g., CH3MgBr) or an organolithium reagent, followed by acidic workup to yield 3-methylbutan-2-ol.

Step 3: Oxidize 3-methylbutan-2-ol to form 3-methylbutan-2-one. Use an oxidizing agent such as PCC or Jones reagent to convert the secondary alcohol into a ketone.

Step 4: Perform a haloform reaction to convert 3-methylbutan-2-one into 2-methylbutanoic acid. This reaction involves treating the ketone with excess halogen (e.g., I2 or Br2) in the presence of a base (e.g., NaOH), followed by acidification to yield the carboxylic acid.

Step 5: Purify the 2-methylbutanoic acid product using techniques such as recrystallization or distillation, depending on the physical properties of the compound.

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Key Concepts

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

Carboxylic Acid Synthesis

Carboxylic acids can be synthesized through various methods, including oxidation of alcohols. In this case, butan-2-ol can be oxidized to form a carboxylic acid. Understanding the reaction conditions and reagents required for oxidation is crucial for successful synthesis.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state, often resulting in the formation of carbonyl compounds or carboxylic acids from alcohols. For butan-2-ol, a common oxidizing agent like potassium dichromate or chromium trioxide can facilitate this transformation.

Rearrangement and Isomerization

In organic synthesis, rearrangement and isomerization can lead to the formation of different structural isomers. The target compound, 2-methylbutanoic acid, suggests that the synthesis may involve a rearrangement of the carbon skeleton during the oxidation process, which is essential to achieve the desired product.

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Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(d)

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(a) PhCH₂CH₂OH → PhCH₂CH₂COOH

Textbook Question

When a chemist attempted the following reaction sequence, the desired product was not formed.

(a) Why?

(b) Suggest a solution to the problem. [Think about chemistry from the end of Chapter 13.]

Textbook Question

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

Textbook Question

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(f) allyl iodide → but-3-enoic acid

Multiple Choice

Which of the following best describes the carboxylation phase of the Calvin cycle?

Multiple Choice

Determine the major product for the following reaction.

Multiple Choice

Predict the major, organic product for the following reaction.

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Show how you would synthesize the following carboxylic acids, using the indicated starting materials.(d) butan-2-ol → 2-methylbutanoic acid

Key Concepts

Carboxylic Acid Synthesis

Oxidation Reactions

Rearrangement and Isomerization

Watch next

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(d) butan-2-ol → 2-methylbutanoic acid