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

Naming Anhydrides

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Naming Anhydrides

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9:22 minutes

Problem 1m,n

Textbook Question

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(m)
(n)

Verified step by step guidance

Step 1: Analyze the first structure (m). The molecule contains a four-membered cyclic structure with two carbonyl groups attached. This is a cyclic anhydride derived from a dicarboxylic acid. To name it, identify the parent dicarboxylic acid and replace 'acid' with 'anhydride' for the common name. For the IUPAC name, use the systematic name of the parent dicarboxylic acid and add 'anhydride'.

Step 2: For the common name of structure (m), recognize that the parent dicarboxylic acid is succinic acid (butane-1,4-dioic acid). Replace 'acid' with 'anhydride' to get 'succinic anhydride'.

Step 3: For the IUPAC name of structure (m), use the systematic name of the parent dicarboxylic acid, which is butane-1,4-dioic acid. Replace 'acid' with 'anhydride' to get 'butane-1,4-dioic anhydride'.

Step 4: Analyze the second structure (n). The molecule contains a cyclopentane ring with two substituents: a hydroxyl group (-OH) and a nitrile group (-CN). Determine the priority of functional groups according to IUPAC rules. The nitrile group has higher priority than the hydroxyl group.

Step 5: For the IUPAC name of structure (n), assign the nitrile group as the main functional group and the hydroxyl group as a substituent. Number the cyclopentane ring to give the nitrile group the lowest possible number. The name will be '2-hydroxycyclopentanecarbonitrile'. For the common name, describe it as 'hydroxycyclopentanecarbonitrile'.

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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 can be derived from carboxylic acids by replacing the hydroxyl group (-OH) with another functional group. Common derivatives include esters, amides, anhydrides, and acyl chlorides. Understanding these derivatives is crucial for naming and identifying their structures, as they exhibit distinct reactivity and properties based on their functional groups.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming chemical compounds, ensuring that each name conveys specific information about the structure and functional groups present. For carboxylic acid derivatives, the IUPAC name typically reflects the parent acid and the substituents or modifications made to it. Familiarity with IUPAC rules is essential for accurately naming compounds and communicating chemical information.

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 carboxylic acid derivatives, common functional groups include carbonyls (C=O), hydroxyls (–OH), and others that influence the compound's reactivity and properties. Recognizing these groups is vital for understanding the behavior and classification of organic compounds.

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