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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4:27 minutes

Problem 33

Textbook Question

When it is strongly heated, ethyl diazoacetate decomposes to give nitrogen gas and a carbene. Draw a Lewis structure of the carbene.

Verified step by step guidance

Identify the structure of ethyl diazoacetate from the image. It consists of a diazo group (N2) attached to a carbon, which is also connected to an ester group.

Understand that upon heating, ethyl diazoacetate decomposes to release nitrogen gas (N2), leaving behind a carbene. The diazo group is responsible for this decomposition.

Focus on the carbon atom that is directly attached to the diazo group. This carbon will become the carbene after the nitrogen gas is released.

Draw the Lewis structure of the carbene. A carbene is a neutral species with a divalent carbon atom that has two non-bonded electrons. Represent the carbon with two single bonds and a pair of dots indicating the lone pair of electrons.

Ensure that the carbene carbon is shown with only six electrons in its valence shell, reflecting its divalent nature. This includes the two electrons from the lone pair and the electrons from the two single bonds.

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Key Concepts

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

Carbene

A carbene is a reactive intermediate in organic chemistry characterized by a carbon atom with only six valence electrons, resulting in a divalent state. This species typically has a neutral charge and can exist in two forms: singlet (with paired electrons) and triplet (with unpaired electrons). Carbenes are highly reactive and can participate in various chemical reactions, including insertion into C-H bonds and cyclopropanation.

Decomposition Reaction

A decomposition reaction is a type of chemical reaction where a single compound breaks down into two or more simpler products. In the case of ethyl diazoacetate, heating causes it to decompose into nitrogen gas and a carbene. This process is often endothermic and can be driven by heat, light, or other forms of energy, leading to the formation of reactive intermediates.

Lewis Structures

Lewis structures are diagrams that represent the bonding between atoms in a molecule and the lone pairs of electrons that may exist. They are essential for visualizing the arrangement of electrons and understanding molecular geometry. In drawing a Lewis structure for a carbene, it is crucial to depict the carbon atom with a double bond to another atom and two unshared electrons, illustrating its unique electronic configuration.

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Related Practice

Textbook Question

Show how you would accomplish each of the following synthetic conversions.

a. trans-but-2-ene → trans-1,2-dimethylcyclopropane

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(g)

Textbook Question

Propose mechanisms consistent with the following reactions.

(d)

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

m. CHBr₃ and 50% aq. NaOH

Textbook Question

Show how you would accomplish each of the following synthetic conversions.

(c)

Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH₂.

(f) Cyclopropanation of (E)- and (Z)-3-methylhex-3-ene gives two different products. Rationalize this outcome.

Textbook Question

Suggest a mechanism for the reaction shown in Figure 16.30 using IZnCH₂I as the cyclopropanating reagent.

Textbook Question

Two chemists at Dupont found that ICH₂ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.

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