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

10. Addition Reactions

Carbene

Organic Chemistry

10. Addition Reactions

Carbene

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3:56 minutes

Problem 92b

Textbook Question

Dichlorocarbene can also be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction.

Verified step by step guidance

Step 1: Begin by identifying the starting material, sodium trichloroacetate (NaO−CCl3). This compound contains a trichloromethyl group attached to a carboxylate functional group.

Step 2: Upon heating, the carboxylate group undergoes decarboxylation. This process involves the loss of carbon dioxide (CO2), which is facilitated by the thermal energy provided.

Step 3: The decarboxylation results in the formation of a trichloromethyl anion (CCl3−). This intermediate is highly unstable and undergoes further reaction.

Step 4: The trichloromethyl anion (CCl3−) eliminates a chloride ion (Cl−), leading to the generation of dichlorocarbene (:CCl2). Dichlorocarbene is a reactive intermediate with a divalent carbon atom and two lone pairs.

Step 5: The final products of the reaction are dichlorocarbene (:CCl2), carbon dioxide (CO2), and sodium chloride (NaCl). The mechanism highlights the thermal decomposition and rearrangement steps leading to the formation of these products.

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Key Concepts

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

Dichlorocarbene Generation

Dichlorocarbene (Br2C:) is a reactive intermediate formed during certain organic reactions. It can be generated from precursors like sodium trichloroacetate through thermal decomposition. The process involves the loss of carbon dioxide (CO2) and the formation of the dichlorocarbene species, which is crucial for various synthetic applications in organic chemistry.

Thermal Decomposition

Thermal decomposition is a chemical reaction where a compound breaks down into simpler substances when heated. In the context of sodium trichloroacetate, heating induces the cleavage of bonds, leading to the release of CO2 and the formation of dichlorocarbene. Understanding this concept is essential for predicting the products of reactions involving heat.

Mechanism of Reaction

A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. For the generation of dichlorocarbene from sodium trichloroacetate, the mechanism involves bond breaking and formation, which can be illustrated through curved arrows in reaction diagrams. Analyzing the mechanism helps in understanding the stability and reactivity of intermediates.

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