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

Acid Chloride Nomenclature

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid Chloride Nomenclature

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4:57 minutes

Problem 1o,p

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the first structure (o). The molecule contains a cyclohexane ring with two substituents: a carboxylic acid group (-COOH) and a nitrile group (-CN). Both substituents are attached to the ring at different positions and are in a trans configuration (opposite sides of the ring).

Step 2: Determine the IUPAC name for the first structure (o). The carboxylic acid group takes priority in naming due to its higher precedence in functional group hierarchy. Number the ring starting from the carbon attached to the carboxylic acid group, ensuring the nitrile group gets the lowest possible number. The name will include 'cyclohexane' as the parent chain, with 'carboxylic acid' and 'nitrile' as substituents.

Step 3: Assign the common name for the first structure (o). Common names often use simpler naming conventions. For example, the carboxylic acid group might be referred to as 'cyclohexanecarboxylic acid,' and the nitrile group as 'cyclohexanenitrile.'

Step 4: Analyze the second structure (p). The molecule contains a benzene ring with two substituents: a bromine atom (-Br) and an acyl chloride group (-COCl). The acyl chloride group is attached directly to the benzene ring, and the bromine atom is positioned at a different location.

Step 5: Determine the IUPAC and common names for the second structure (p). For the IUPAC name, the acyl chloride group takes priority, and the bromine atom is treated as a substituent. Number the benzene ring starting from the carbon attached to the acyl chloride group, ensuring the bromine atom gets the lowest possible number. The name will include 'benzoyl chloride' for the acyl chloride group and 'bromo' for the bromine substituent. The common name might simply refer to the molecule as 'bromobenzoyl chloride.'

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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 one or more carboxyl groups (-COOH). They are known for their acidic properties due to the ability of the carboxyl group to donate a proton (H+). Common examples include acetic acid and benzoic acid. Understanding their structure and reactivity is essential for naming derivatives.

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, and acyl chlorides. Each derivative has distinct properties and reactivity patterns, which are crucial for proper naming and understanding their chemical behavior.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for naming based on the structure of the molecule, including the longest carbon chain, functional groups, and substituents. Familiarity with IUPAC rules is essential for accurately naming carboxylic acid derivatives and understanding their relationships to parent compounds.

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