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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1:55 minutes

Problem 41a,b,c(i)

Textbook Question

For each heterocyclic compound,
(i) explain what type of acid derivative is present.
(a)
(b)
(c)

Verified step by step guidance

Step 1: Analyze compound A. The structure contains a benzene ring fused to a five-membered ring with two carbonyl groups. This indicates that compound A is a cyclic anhydride, specifically a phthalic anhydride derivative.

Step 2: Analyze compound B. The structure contains a six-membered ring with one sulfur atom and a carbonyl group attached to the ring. This suggests that compound B is a thioester derivative, where the sulfur atom replaces the oxygen typically found in esters.

Step 3: Analyze compound C. The structure contains a five-membered ring with a nitrogen atom and a carbonyl group attached to the ring. This indicates that compound C is a lactam, which is a cyclic amide.

Step 4: Understand the general classification of acid derivatives. Acid derivatives include anhydrides, esters, thioesters, amides, and lactams, all of which are derived from carboxylic acids by replacing the hydroxyl group (-OH) with another functional group.

Step 5: Relate the functional groups in each compound to their respective acid derivative types. Compound A is an anhydride, compound B is a thioester, and compound C is a lactam, based on the presence of specific functional groups in their structures.

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Key Concepts

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

Heterocyclic Compounds

Heterocyclic compounds are cyclic structures that contain at least one atom in the ring that is not carbon, such as nitrogen, oxygen, or sulfur. These compounds are significant in organic chemistry due to their diverse chemical properties and biological activities. Understanding the nature of the heteroatoms and their influence on the compound's reactivity is crucial for analyzing their acid derivatives.

Acid Derivatives

Acid derivatives are compounds that are derived from carboxylic acids by replacing the hydroxyl group (-OH) with another functional group. Common types include esters, amides, and anhydrides. Identifying the type of acid derivative present in a heterocyclic compound involves recognizing the functional groups attached to the heterocycle and understanding their reactivity and properties.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of heterocyclic compounds, common functional groups include carbonyls, amines, and thiols. Recognizing these groups is essential for determining the type of acid derivative and predicting the compound's behavior in chemical reactions.

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Related Practice

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(c)

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(d)

Textbook Question

Peroxyacetic acid (bp = 105 °C) has a lower boiling point than acetic acid (bp = 118 °C), even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.

Multiple Choice

Which of the following is NOT a carboxylic acid derivative?

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,