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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enamine Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enamine Alkylation and Acylation

Previous problemNext problem

3:52 minutes

Problem 69e

Textbook Question

Predict the products of the following reactions.
(e)

Verified step by step guidance

Step 1: Analyze the starting material. The molecule contains a nitrogen atom in a pyrrolidine ring, which is nucleophilic due to the lone pair on nitrogen. Additionally, the molecule has a conjugated diene system with phenyl substituents.

Step 2: Examine the reagents. The first reagent is a phenyl-substituted allyl bromide (Ph-CH=CH-CH2Br), which is an electrophile due to the bromine atom. The second reagent is H3O+, which indicates acidic conditions.

Step 3: Predict the first step of the reaction. The nucleophilic nitrogen in the pyrrolidine ring will attack the electrophilic carbon in the allyl bromide, displacing the bromine atom via an SN2 mechanism. This forms a new bond between the nitrogen and the allyl group.

Step 4: Consider the role of H3O+. Under acidic conditions, the newly formed nitrogen-allyl bond may undergo protonation, leading to further rearrangements or stabilization of the product. Additionally, the conjugated diene system may remain intact or participate in further reactions depending on the conditions.

Step 5: Predict the final product. The reaction likely results in a nitrogen-substituted allyl compound, with the pyrrolidine ring intact and the conjugated diene system preserved. The exact structure depends on the stability of intermediates under acidic conditions.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Enamines

Enamines are derivatives of imines, formed by the reaction of an aldehyde or ketone with a secondary amine. They contain a carbon-nitrogen double bond and are highly reactive intermediates in organic synthesis. Enamines can undergo nucleophilic addition reactions, making them useful for alkylation and acylation processes.

Alkylation

Alkylation is a chemical reaction that involves the transfer of an alkyl group from one molecule to another. In the context of enamines, alkylation typically occurs when the nucleophilic carbon of the enamine attacks an electrophile, such as an alkyl halide. This process is crucial for building complex organic molecules and expanding carbon chains.

Acid-Catalyzed Hydrolysis

Acid-catalyzed hydrolysis is a reaction where water is used to break chemical bonds in the presence of an acid catalyst, often leading to the formation of alcohols or carbonyl compounds. In the case of enamines, treatment with an acid like H3O+ can convert the enamine back to the corresponding carbonyl compound, facilitating the synthesis of various functional groups.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning