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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Multiple Choice

Predict the product of the reaction

Chemical structure of a primary alcohol with a hydroxyl group.

Chemical structure of a ketone with a carbonyl group.

Chemical structure of a carbonyl compound with an oxygen atom.

Chemical structure of a secondary alcohol with a hydroxyl group.

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Verified step by step guidance

The first step involves the reaction of the alkyl bromide with lithium in THF. This is a metal-halogen exchange reaction where the bromine atom is replaced by lithium, forming an organolithium reagent. The organolithium reagent is highly nucleophilic.

Next, the organolithium reagent reacts with acetone. Acetone is a ketone, and the organolithium acts as a nucleophile, attacking the carbonyl carbon of acetone. This forms an alkoxide intermediate.

The alkoxide intermediate is then protonated by the addition of NH4Cl, which provides a source of protons. This step converts the alkoxide into an alcohol.

The final product is an alcohol where the original alkyl group from the bromide is now attached to the carbon that was part of the carbonyl group in acetone.

Throughout these steps, the stereochemistry and regiochemistry should be considered, ensuring that the nucleophilic attack occurs at the less hindered side of the carbonyl group, if applicable.