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

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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Problem 48b

Textbook Question

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.
(b)

Verified step by step guidance

Step 1: Identify the functional groups in the reactant and product. The reactant contains an ester group attached to a pyrrole ring, while the product has an additional alkyl group attached to the pyrrole ring.

Step 2: Recognize that a cuprate reagent can be used for conjugate addition to introduce an alkyl group. Cuprate reagents are typically organocopper compounds, such as R2CuLi, where R is an alkyl group.

Step 3: Use the cuprate reagent to perform a conjugate addition to the pyrrole ring. This involves the nucleophilic attack of the cuprate reagent on the electrophilic site of the pyrrole ring, resulting in the formation of a new carbon-carbon bond.

Step 4: Consider the stereochemistry and regiochemistry of the addition. Ensure that the alkyl group is added to the correct position on the pyrrole ring as indicated in the product structure.

Step 5: Perform any necessary work-up steps to isolate and purify the product, such as quenching the reaction, washing, and drying the organic layer.

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Key Concepts

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

Cuprate Reagents

Cuprate reagents, typically organocuprates, are organometallic compounds containing copper. They are highly nucleophilic and are commonly used in organic synthesis to form carbon-carbon bonds. Cuprates can react with various electrophiles, making them versatile in transforming functional groups in organic molecules.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, replacing a leaving group. This process is crucial for converting functional groups and is often categorized into two main types: SN1 and SN2, depending on the reaction conditions and the structure of the substrate.

Reaction Mechanism

A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. Understanding the mechanism is essential for predicting the products of a reaction, optimizing conditions, and designing synthetic pathways. Each step in a mechanism involves specific interactions between reactants, intermediates, and products.

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