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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4:44 minutes

Problem 41e

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)

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 double bonds, which is pyrrole. Additionally, it has a hydroxyl (-OH) group attached to the ring.

Step 2: Determine the type of acid derivative present. The hydroxyl group (-OH) attached to the pyrrole ring indicates that this compound is an alcohol derivative rather than a typical acid derivative like esters, amides, or anhydrides.

Step 3: Predict the products of complete hydrolysis. Since the compound is an alcohol derivative, hydrolysis would not break the ring but could involve reactions with the hydroxyl group, potentially leading to oxidation or other transformations depending on the conditions.

Step 4: Assess aromaticity. Pyrrole is aromatic because it satisfies Huckel's rule (4n+2 π electrons, where n=1). The lone pair on the nitrogen contributes to the π-electron system, making a total of 6 π electrons in the conjugated ring system.

Step 5: Explain aromaticity further. The ring is planar, fully conjugated, and cyclic, allowing delocalization of π electrons across the ring. These characteristics confirm the aromatic nature of pyrrole.

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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 a carbon atom, typically nitrogen, oxygen, or sulfur. These compounds can exhibit unique chemical properties due to the presence of these heteroatoms, influencing their reactivity and interactions. Understanding the structure of heterocycles is crucial for identifying their functional groups and predicting their behavior in chemical reactions.

Acid Derivatives

Acid derivatives are compounds that are derived from carboxylic acids by replacing the hydroxyl group (-OH) with another functional group. Common examples include esters, amides, and anhydrides. In the context of the question, recognizing the type of acid derivative present in the heterocyclic compound is essential for predicting the products of hydrolysis and understanding the compound's reactivity.

Aromaticity

Aromaticity refers to the property of cyclic compounds that exhibit enhanced stability due to the delocalization of π-electrons across the ring structure, following Huckel's rule (4n + 2 π-electrons). Aromatic compounds are typically planar and have a continuous overlap of p-orbitals. Determining whether a heterocyclic compound is aromatic is important for understanding its chemical behavior and stability, especially in reactions involving electrophiles.