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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4:49 minutes

Problem 41f

Textbook Question

For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(ii) show what compounds would result from complete hydrolysis.
(iii) are any of the rings aromatic? Explain.
(f)

Verified step by step guidance

Step 1: Identify the heterocyclic compound. The given structure is a five-membered ring containing one nitrogen atom and two oxygen atoms. The functional group present is an amide group (-CONH-), which is a derivative of a carboxylic acid.

Step 2: Determine the products of complete hydrolysis. Hydrolysis of an amide involves breaking the bond between the carbonyl carbon and the nitrogen atom. This reaction typically yields a carboxylic acid and an amine. In this case, hydrolysis would produce a carboxylic acid (likely formic acid or acetic acid depending on the substituents) and ammonia (NH₃).

Step 3: Assess aromaticity. To determine if the ring is aromatic, apply Huckel's rule, which states that a compound is aromatic if it is cyclic, planar, fully conjugated, and contains (4n + 2) π electrons. The given compound does not meet these criteria because the nitrogen atom in the amide group disrupts conjugation, and the ring does not have a continuous π-electron system. Therefore, the ring is not aromatic.

Step 4: Explain the acid derivative classification. The compound is classified as an amide, which is a derivative of a carboxylic acid where the hydroxyl group (-OH) of the acid is replaced by an amino group (-NH₂).

Step 5: Summarize the findings. The compound is a non-aromatic amide, and upon hydrolysis, it yields a carboxylic acid and ammonia. The ring structure itself does not exhibit aromaticity due to the lack of a fully conjugated π-electron system.

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Key Concepts

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

Carboxylic Acid Derivatives

Carboxylic acid derivatives are compounds that contain the carboxyl group (–COOH) or are derived from carboxylic acids by replacing the hydroxyl group with another functional group. Common derivatives include esters, amides, and anhydrides. In the provided structure, the presence of the amine group (–NH2) indicates that it is an amide, which is formed from the reaction of a carboxylic acid with an amine.

Hydrolysis of Amides

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. For amides, complete hydrolysis typically yields a carboxylic acid and an amine or ammonia. In the case of the given compound, hydrolysis would result in the formation of a carboxylic acid and an amine, illustrating the transformation of the amide back to its parent acid and amine.

Aromaticity

Aromaticity refers to the property of cyclic compounds that exhibit enhanced stability due to the delocalization of π-electrons across the ring structure. For a compound to be aromatic, it must follow Hückel's rule, which states that it should have (4n + 2) π-electrons, where n is a non-negative integer. In the provided structure, the cyclic ring is likely aromatic if it meets these criteria, contributing to its stability and reactivity.

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Related Practice

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.).

(c)

(d)

Textbook Question

Which of the following are considered carboxylic acid derivatives?

(a)

Textbook Question

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(d)

Textbook Question

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(e)

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)

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For each heterocyclic compound,(i) explain what type of acid derivative is present.(ii) show what compounds would result from complete hydrolysis.(iii) are any of the rings aromatic? Explain.(f)

Key Concepts

Carboxylic Acid Derivatives

Hydrolysis of Amides

Aromaticity

Watch next

For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(ii) show what compounds would result from complete hydrolysis.
(iii) are any of the rings aromatic? Explain.
(f)