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

25. Condensation Chemistry

Conjugate Addition

Organic Chemistry

25. Condensation Chemistry

Conjugate Addition

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4:54 minutes

Problem 66i

Textbook Question

What are the products of the following reactions?
i.

Verified step by step guidance

Step 1: Identify the reactants. Ethyl acrylate is an ester with an α,β-unsaturated carbonyl group, and ethanamine is a primary amine.

Step 2: Recognize the type of reaction. This is a nucleophilic addition reaction where the amine (ethanamine) acts as a nucleophile and attacks the electrophilic carbon of the α,β-unsaturated carbonyl group in ethyl acrylate.

Step 3: Analyze the mechanism. The lone pair of electrons on the nitrogen atom of ethanamine attacks the β-carbon of the double bond in ethyl acrylate, leading to the formation of a new bond. This breaks the π-bond of the alkene and forms an intermediate.

Step 4: Consider proton transfer. After the nucleophilic attack, proton transfer occurs to stabilize the intermediate, resulting in the formation of a β-amino ester.

Step 5: Write the product structure. The final product is a β-amino ester where the ethyl acrylate has been modified by the addition of ethanamine at the β-carbon position.

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Key Concepts

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

Conjugate Addition

Conjugate addition refers to the reaction where a nucleophile adds to the β-carbon of an α,β-unsaturated carbonyl compound. In this case, ethanamine acts as the nucleophile, attacking the β-carbon of ethyl acrylate, leading to the formation of a new bond. This reaction is crucial in organic synthesis as it allows for the formation of more complex molecules.

Nucleophiles and Electrophiles

In organic chemistry, nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. In the given reaction, ethanamine (a nucleophile) attacks the electrophilic carbon of ethyl acrylate, facilitating the conjugate addition process. Understanding the roles of nucleophiles and electrophiles is essential for predicting reaction outcomes.

Reaction Mechanism

A reaction mechanism outlines the step-by-step process by which reactants transform into products. For the reaction between ethyl acrylate and ethanamine, the mechanism involves the nucleophilic attack of ethanamine on the β-carbon of the acrylate, followed by proton transfer and stabilization of the resulting intermediate. Grasping the mechanism is vital for understanding how and why specific products are formed.

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What are the products of the following reactions?i.

Key Concepts

Conjugate Addition

Nucleophiles and Electrophiles

Reaction Mechanism

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What are the products of the following reactions?
i.