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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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2:41 minutes

Problem 7a

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(a)

Verified step by step guidance

Step 1: Analyze the starting material and product. The starting material is benzoic acid (C₆H₅COOH), and the product is acetophenone (C₆H₅COCH₃). This transformation involves replacing the carboxylic acid group (-COOH) with a ketone group (-COCH₃).

Step 2: Prepare the organolithium reagent. To introduce the methyl group (-CH₃) in the ketone, use methyl lithium (CH₃Li) as the organolithium reagent. Organolithium reagents are highly nucleophilic and react with electrophilic centers.

Step 3: React the benzoic acid with the organolithium reagent. The carboxylic acid group (-COOH) reacts with CH₃Li to form an intermediate. The acidic proton of the carboxylic acid is replaced by the lithium ion, forming a lithium carboxylate intermediate.

Step 4: Perform a second addition of the organolithium reagent. The lithium carboxylate intermediate reacts further with another equivalent of CH₃Li, leading to the formation of a dianion intermediate. This intermediate undergoes rearrangement to form the ketone product.

Step 5: Quench the reaction. After the organolithium reagent has reacted completely, the reaction mixture is quenched with water or a mild acid to neutralize any remaining reactive species and isolate the acetophenone product.

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Key Concepts

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

Organolithium Reagents

Organolithium reagents are highly reactive compounds containing a carbon-lithium bond. They are used as strong nucleophiles in organic synthesis, capable of attacking electrophiles such as carbonyls and halides. Their reactivity allows them to form new carbon-carbon bonds, making them essential for various synthetic transformations.

Acid-Base Reactions

In organic chemistry, acid-base reactions involve the transfer of protons (H+) between species. When an organolithium reagent is added to an acid, it can deprotonate the acid, generating a carbanion. This step is crucial for initiating further reactions, as the resulting carbanion can act as a nucleophile in subsequent steps.

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. Understanding the mechanism of how organolithium reagents interact with acids is vital for designing efficient synthetic routes. This includes recognizing the intermediates formed and the conditions required for successful conversions.

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