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

Enolate Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

Previous problemNext problem

2:37 minutes

Problem 49c

Textbook Question

Draw the products of the following reactions:
c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

Verified step by step guidance

Step 1: Identify the role of LDA (Lithium Diisopropylamide) in the reaction. LDA is a strong, non-nucleophilic base that is used to deprotonate the alpha-hydrogen of acetone, forming an enolate ion. This enolate is highly nucleophilic and will participate in subsequent reactions.

Step 2: Recognize the slow addition of ethyl acetate. Ethyl acetate is an ester, and its carbonyl group is electrophilic. The enolate ion formed from acetone will attack the carbonyl carbon of ethyl acetate in a nucleophilic addition reaction, forming a new carbon-carbon bond.

Step 3: Understand the intermediate formed after the nucleophilic attack. The product of this step will be a beta-keto ester, where the acetone enolate has added to the ethyl acetate molecule. This intermediate will have both a ketone and an ester functional group.

Step 4: Analyze the role of HCl in the second step. HCl is an acid that will protonate the intermediate, stabilizing it and completing the reaction. This step ensures the final product is neutral and fully formed.

Step 5: Draw the final product. The final product will be a beta-keto ester, specifically ethyl 3-oxobutanoate, formed by the addition of acetone enolate to ethyl acetate followed by protonation with HCl.

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.

Enolate Formation

Enolate formation is a key step in reactions involving carbonyl compounds, where a base abstracts a proton from the alpha carbon, resulting in a resonance-stabilized enolate ion. In this reaction, LDA (Lithium diisopropylamide) acts as a strong base to deprotonate acetone, generating the enolate that can subsequently react with electrophiles like ethyl acetate.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in carbonyl compounds. In this case, the enolate formed from acetone acts as a nucleophile and attacks the carbonyl carbon of ethyl acetate, leading to the formation of a beta-hydroxy carbonyl compound.

Acid Workup

An acid workup is a common procedure in organic synthesis that involves adding an acid, such as HCl, to neutralize the reaction mixture and protonate any basic species. After the nucleophilic addition of the enolate to ethyl acetate, the addition of HCl helps to stabilize the product and convert any remaining enolate or intermediate into the final carbonyl product, facilitating purification.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning