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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6:12 minutes

Problem 7d

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one

Verified step by step guidance

Step 1: Begin by understanding the target transformation. The goal is to convert phenylacetic acid (C₆H₅CH₂COOH) into 3,3-dimethyl-1-phenylbutan-2-one. This involves adding a new carbon chain and introducing a ketone functional group.

Step 2: Convert phenylacetic acid into a more reactive intermediate. Use a reagent like thionyl chloride (SOCl₂) to transform the carboxylic acid group (-COOH) into an acid chloride (-COCl). This step increases the electrophilicity of the carbonyl carbon, making it more reactive toward nucleophiles.

Step 3: Prepare the organolithium reagent. To introduce the 3,3-dimethyl group, synthesize tert-butyllithium ((CH₃)₃CLi) by reacting tert-butyl bromide ((CH₃)₃CBr) with lithium metal. This organolithium reagent will act as a nucleophile in the next step.

Step 4: Perform the nucleophilic addition. React the acid chloride (C₆H₅CH₂COCl) with tert-butyllithium ((CH₃)₃CLi). The organolithium reagent will attack the carbonyl carbon of the acid chloride, forming a tetrahedral intermediate. This intermediate will collapse, expelling the chloride ion (Cl⁻) and forming a ketone.

Step 5: Verify the structure of the product. The final compound, 3,3-dimethyl-1-phenylbutan-2-one, should have the phenyl group (C₆H₅) attached to the 1-position, a ketone group at the 2-position, and two methyl groups at the 3-position. Ensure the reaction conditions are optimized to achieve the desired 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 act as strong nucleophiles in organic synthesis, allowing for the formation of carbon-carbon bonds. In the context of the question, they can be used to add alkyl groups to carbonyl compounds, facilitating the transformation of phenylacetic acid into more complex structures.

Acid-Base Reactions

Acid-base reactions are fundamental chemical processes where an acid donates a proton (H+) and a base accepts it. In organic synthesis, the reactivity of acids can be exploited to generate reactive intermediates. When phenylacetic acid reacts with an organolithium reagent, it can deprotonate, leading to the formation of a carbanion that can further react with electrophiles to create desired products.

Carbonyl Chemistry

Carbonyl chemistry involves the study of compounds containing a carbonyl group (C=O), which is a key functional group in organic molecules. Carbonyl compounds, such as ketones and aldehydes, are pivotal in synthetic transformations. In this case, the reaction of the carbanion generated from phenylacetic acid with a suitable electrophile can lead to the formation of the target ketone, 3,3-dimethyl-1-phenylbutan-2-one.

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