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

Carboxylic Acid Derivatives

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid Derivatives

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1:48 minutes

Problem 55e

Textbook Question

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.
(e) heptanoic acid

Verified step by step guidance

Identify the target molecule (octan-2-one) and analyze its structure. It is a ketone with the carbonyl group on the second carbon of an eight-carbon chain.

Examine the starting material (heptanoic acid). It is a carboxylic acid with a seven-carbon chain. To synthesize octan-2-one, you need to extend the carbon chain by one carbon and introduce a ketone group at the second position.

Convert heptanoic acid to heptanoyl chloride using a reagent like thionyl chloride (SOCl₂) or oxalyl chloride. This step activates the carboxylic acid for further reactions.

Perform a Friedel-Crafts acylation reaction using heptanoyl chloride and ethylbenzene in the presence of a Lewis acid catalyst like AlCl₃. This step introduces the additional carbon to form the ketone group at the desired position.

Finally, perform a hydrolysis or reduction step if necessary to remove any protecting groups or side products, ensuring the final product is octan-2-one.

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Key Concepts

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

Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are important in organic synthesis due to their ability to undergo various reactions, such as esterification and reduction. In the context of synthesizing octan-2-one from heptanoic acid, understanding how to manipulate the carboxylic acid functional group is crucial for forming the desired ketone.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In organic chemistry, this often refers to the conversion of carbonyl compounds (like carboxylic acids) to alcohols or ketones. For synthesizing octan-2-one from heptanoic acid, a reduction step may be necessary to convert the carboxylic acid into a suitable intermediate that can then be transformed into the ketone.

Rearrangement Reactions

Rearrangement reactions involve the reorganization of the molecular structure of a compound, often resulting in the formation of a different functional group or isomer. In the synthesis of octan-2-one, a rearrangement may be required to shift the carbon skeleton from heptanoic acid to the desired ketone structure. Understanding how to apply rearrangement mechanisms is essential for achieving the target compound.

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Related Practice

Textbook Question

Predict the products (if any) of the following acid–base reactions.

(a) acetic acid + ammonia

(b) phthalic acid + excess NaOH

Textbook Question

Arrange each group of compounds in order of increasing acidity.

(a) phenol, ethanol, acetic acid

(b) p-toluenesulfonic acid, acetic acid, chloroacetic acid

(d) butyric acid, α-bromobutyric acid, β-bromobutyric acid

(e)

Textbook Question

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) Determine the kind of polymer (polyamide, polyester, etc.).

(ii) Draw the structures of the monomers that would be released by complete hydrolysis.

(iii) Suggest what monomers or stable derivatives of the monomers might be used to make these polymers.

(a)

Textbook Question

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) Determine the kind of polymer (polyamide, polyester, etc.).

(ii) Draw the structures of the monomers that would be released by complete hydrolysis.

(iii) Suggest what monomers or stable derivatives of the monomers might be used to make these polymers.

(b)

Textbook Question

(A true story.) Chemistry lab students added an excess of ethylmagnesium bromide to methyl furoate, expecting the Grignard reagent to add twice and form the tertiary alcohol. After water workup, they found that the product was a mixture of two compounds. One was the expected product having two ethyl groups, but the unexpected product had added three ethyl groups. Propose a mechanism to explain the formation of the unexpected product.

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(e)

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(g)

Textbook Question

Show how you would convert the following starting materials to the indicated nitriles:

(b) phenylacetic acid → 3-phenylpropionitrile

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Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.(e) heptanoic acid

Key Concepts

Carboxylic Acids

Reduction Reactions

Rearrangement Reactions

Watch next

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.
(e) heptanoic acid