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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4:11 minutes

Problem 7

Textbook Question

Predict the product that would result from the reaction of an organolithium reagent with a ketone when a hydroxyl group is present in the ketone substrate.

Verified step by step guidance

Identify the functional groups present in the ketone substrate. You have a ketone group (C=O) and a hydroxyl group (-OH).

Understand the reactivity of organolithium reagents. Organolithium compounds are strong nucleophiles and bases, capable of attacking electrophilic centers such as the carbonyl carbon in ketones.

Consider the interaction between the organolithium reagent and the ketone. The organolithium reagent will attack the electrophilic carbon of the carbonyl group, leading to the formation of an alkoxide intermediate.

Recognize the role of the hydroxyl group. The presence of a hydroxyl group can lead to protonation of the alkoxide intermediate, resulting in the formation of an alcohol.

Predict the final product. The reaction typically results in the formation of a tertiary alcohol, where the organolithium reagent adds to the ketone, and the hydroxyl group stabilizes the intermediate.

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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 used in organic synthesis, characterized by a carbon-lithium bond. They act as strong nucleophiles and bases, capable of attacking electrophilic centers such as carbonyl groups in ketones, leading to the formation of alcohols after subsequent protonation.

Ketone Reactivity

Ketones contain a carbonyl group (C=O) that is electrophilic, making them susceptible to nucleophilic attack. In reactions with organolithium reagents, the nucleophile attacks the carbonyl carbon, resulting in the formation of an alkoxide intermediate, which is then protonated to yield an alcohol product.

Hydroxyl Group Influence

The presence of a hydroxyl group in the ketone substrate can influence the reaction pathway. Hydroxyl groups can act as proton donors, facilitating the protonation of the alkoxide intermediate formed after nucleophilic attack. Additionally, they may participate in hydrogen bonding, potentially affecting the reactivity and orientation of the reaction.

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