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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7:52 minutes

Problem 18b

Textbook Question

Cyclopropanation using any of the reagents discussed here is stereospecific.
(b) Draw a reaction coordinate diagram for cyclopropanation.

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Understand the concept of cyclopropanation: Cyclopropanation is a reaction where a three-membered cyclopropane ring is formed by adding a carbene or carbenoid to an alkene. This reaction is stereospecific, meaning the stereochemistry of the starting alkene is preserved in the product.

Identify the key components of a reaction coordinate diagram: A reaction coordinate diagram plots the energy of the system (y-axis) against the progress of the reaction (x-axis). It includes the energy of reactants, transition states, intermediates (if any), and products.

Determine the energy profile for cyclopropanation: Cyclopropanation typically involves a single-step mechanism when using a carbene or carbenoid. The reaction proceeds through a single transition state, so the diagram will show a curve with one peak representing the transition state.

Label the diagram: On the reaction coordinate diagram, label the starting point as 'Reactants' (alkene + carbene/carbenoid), the peak as 'Transition State,' and the endpoint as 'Products' (cyclopropane). Indicate the relative energy levels, with the transition state being the highest energy point.

Indicate stereospecificity: To emphasize the stereospecific nature of the reaction, note that the stereochemistry of the alkene (cis or trans) is preserved in the cyclopropane product. This can be annotated on the diagram or mentioned in accompanying notes.

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Key Concepts

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

Cyclopropanation

Cyclopropanation is a chemical reaction that involves the formation of a cyclopropane ring from an alkene. This reaction typically occurs through the addition of a reagent, such as a carbenoid or a metal-carbene complex, which facilitates the insertion of a three-membered ring into the double bond of the alkene. The stereospecific nature of this reaction means that the configuration of the starting alkene directly influences the stereochemistry of the resulting cyclopropane.

Stereospecificity

Stereospecificity refers to a reaction's ability to produce a specific stereoisomer from a particular stereoisomer of the reactant. In the context of cyclopropanation, this means that if the starting alkene has a certain stereochemistry (e.g., cis or trans), the cyclopropane product will retain that stereochemical relationship. This property is crucial for predicting the outcome of reactions and understanding the mechanisms involved.

Reaction Coordinate Diagram

A reaction coordinate diagram is a graphical representation that illustrates the energy changes during a chemical reaction. It typically plots the potential energy of the system against the progress of the reaction, showing the transition states and intermediates. For cyclopropanation, the diagram would depict the energy barrier for the formation of the cyclopropane ring, highlighting the activation energy required and the stability of the reactants and products.

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Related Practice

Textbook Question

Cyclopropanation using any of the reagents discussed here is stereospecific.

(a) What does this say about the mechanism?

Textbook Question

Predict the product of the following reactions.

(b)

Textbook Question

The following transformation is used as an early step in the synthesis of cilastatin, a drug used to counter antibiotic resistance. Identify a possible reagent for this step.

Textbook Question

Predict the product of the following reactions.

(a)

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.

(h) Of the reactions studied here in Chapter 8, cyclopropanation is most similar to which?

Textbook Question

To determine the stereochemistry of curacin A by synthesis, it would have been necessary to prepare all stereoisomers of the C₁₇―C₂₀ cyclopropane fragment. How would the reaction in Figure 16.30 be modified to produce the other stereoisomers shown here?

Textbook Question

Nitrogen-containing heterocycles form particularly stable carbenes and are commonly used as ligands in organometallic chemistry. (a) Why is the carbene shown particularly stable? [It may be helpful to draw the molecular orbital picture.]

Textbook Question

The reaction of an alkene with diazomethane forms a cyclopropane ring. Propose a mechanism for the reaction. (Hint: It is a concerted reaction.)

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Cyclopropanation using any of the reagents discussed here is stereospecific. (b) Draw a reaction coordinate diagram for cyclopropanation.

Key Concepts

Cyclopropanation

Stereospecificity

Reaction Coordinate Diagram

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Cyclopropanation using any of the reagents discussed here is stereospecific.
(b) Draw a reaction coordinate diagram for cyclopropanation.