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

Decarboxylation Mechanism

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Decarboxylation Mechanism

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2:32 minutes

Problem 52

Textbook Question

Which of the following compounds decarboxylates when heated?

Verified step by step guidance

Step 1: Understand the concept of decarboxylation. Decarboxylation is the removal of a carboxyl group (-COOH) from a molecule, typically releasing carbon dioxide (CO₂). This reaction often occurs in compounds with a β-keto acid or a carboxylic acid group adjacent to a carbonyl group.

Step 2: Analyze compound (i). This compound contains two carboxylic acid groups (-COOH) attached to a cyclohexane ring. However, neither of these carboxylic acid groups is adjacent to a carbonyl group, which is necessary for decarboxylation to occur under heating.

Step 3: Analyze compound (ii). This compound has a carboxylic acid group (-COOH) adjacent to a ketone group (C=O). This structure is characteristic of a β-keto acid, which readily undergoes decarboxylation when heated.

Step 4: Analyze compound (iii). This compound contains a hydroxyl group (-OH) and a carboxylic acid group (-COOH) attached to a cyclohexane ring. However, the carboxylic acid group is not adjacent to a carbonyl group, so it does not decarboxylate under heating.

Step 5: Analyze compound (iv). This compound contains two ketone groups (C=O) attached to a cyclohexane ring but lacks a carboxylic acid group (-COOH). Decarboxylation requires the presence of a carboxylic acid group, so this compound does not undergo decarboxylation.

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Key Concepts

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

Decarboxylation

Decarboxylation is a chemical reaction that involves the removal of a carboxyl group (-COOH) from a molecule, resulting in the release of carbon dioxide (CO2). This process is often facilitated by heat and is common in organic compounds containing carboxylic acids. Understanding the conditions under which decarboxylation occurs is crucial for predicting the behavior of organic compounds when heated.

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 and can undergo various reactions, including decarboxylation. Identifying the presence of carboxylic acid functional groups in the given compounds is essential for determining which compounds are likely to decarboxylate upon heating.

Thermal Stability of Functional Groups

The thermal stability of functional groups refers to their ability to withstand heat without undergoing decomposition or reaction. Different functional groups have varying stabilities; for instance, carboxylic acids can decarboxylate when heated, while other groups may not. Analyzing the structures of the compounds in the question helps assess their thermal stability and predict their behavior under heat.

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