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 Carboxylic Acids

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Naming Carboxylic Acids

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5:36 minutes

Problem 1e-h

Textbook Question

Draw the structures of the following carboxylic acids.
(e) trans-2-methylcyclohexanecarboxylic acid
(f) 2,3-dimethylfumaric acid
(g) m-chlorobenzoic acid
(h) 3-methylphthalic acid

Verified step by step guidance

Step 1: Understand the structure of a carboxylic acid. A carboxylic acid contains a carboxyl group (-COOH) attached to a carbon atom. This functional group is the defining feature of carboxylic acids.

Step 2: For trans-2-methylcyclohexanecarboxylic acid, start with a cyclohexane ring. Add a carboxyl group (-COOH) to one carbon atom of the ring. Then, add a methyl group (-CH₃) to the second carbon atom in a trans configuration relative to the carboxyl group. Ensure the substituents are on opposite sides of the ring plane.

Step 3: For 2,3-dimethylfumaric acid, begin with the structure of fumaric acid, which is a trans isomer of butenedioic acid. Add two methyl groups (-CH₃), one on the second carbon and one on the third carbon of the double bond. Ensure the double bond remains in the trans configuration, with the carboxyl groups (-COOH) on opposite sides of the double bond.

Step 4: For m-chlorobenzoic acid, start with the benzene ring as the base structure. Attach a carboxyl group (-COOH) to one carbon atom of the benzene ring. Then, add a chlorine atom (Cl) to the meta position relative to the carboxyl group. The meta position means there is one carbon atom separating the carboxyl group and the chlorine atom on the ring.

Step 5: For 3-methylphthalic acid, begin with the structure of phthalic acid, which is a benzene ring with two carboxyl groups (-COOH) in the ortho position (adjacent to each other). Add a methyl group (-CH₃) to the third carbon atom of the benzene ring, counting from one of the carboxyl groups. Ensure the positions of all substituents are clearly indicated.

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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+). Understanding the structure and functional group of carboxylic acids is essential for drawing their chemical structures accurately.

Cycloalkanes and Substituents

Cycloalkanes are saturated hydrocarbons with carbon atoms arranged in a ring structure. When substituents, such as methyl groups, are attached to the cycloalkane, their positions can affect the compound's properties and nomenclature. Recognizing how to depict these substituents in relation to the carboxylic acid group is crucial for accurately representing the structures requested in the question.

Nomenclature of Organic Compounds

The nomenclature of organic compounds follows specific rules set by the International Union of Pure and Applied Chemistry (IUPAC). This includes naming conventions for identifying the longest carbon chain, the position of functional groups, and the naming of substituents. Familiarity with these rules is necessary to interpret the names of the acids provided and to draw their correct structures.

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