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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3:53 minutes

Problem 7b

Textbook Question

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

Verified step by step guidance

Step 1: Begin by converting the alkyl bromide (cyclopentyl bromide) into an organolithium reagent. This can be achieved by reacting cyclopentyl bromide with metallic lithium in a dry, inert solvent such as hexane or ether. The reaction forms cyclopentyllithium.

Step 2: Prepare the acid that will react with the organolithium reagent. In this case, the acid should be acetic acid (CH₃COOH), as the target molecule contains a ketone group derived from acetic acid.

Step 3: Add the cyclopentyllithium reagent to acetic acid. The organolithium reagent acts as a nucleophile and attacks the carbonyl carbon of acetic acid, forming an intermediate.

Step 4: Allow the intermediate to undergo proton transfer and rearrangement. This step leads to the formation of the desired ketone product, cyclopentanone.

Step 5: Purify the product using standard organic chemistry techniques such as distillation or recrystallization to isolate the cyclopentanone.

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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 and are commonly used in organic synthesis to form carbon-carbon bonds. In the context of the question, they can react with electrophiles, such as carbonyl compounds, to facilitate the conversion of halogenated cyclic compounds into more complex structures.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, the organolithium reagent acts as the nucleophile, attacking the carbon atom bonded to the bromine atom, leading to the formation of a new carbon-carbon bond and the release of bromide ion as a leaving group.

Formation of Carbonyl Compounds

The formation of carbonyl compounds involves the introduction of a carbonyl functional group (C=O) into a molecule. In the given reaction, the organolithium reagent adds to the cyclic compound, followed by a reaction with an acid to convert the resulting intermediate into a stable carbonyl compound. This transformation is crucial in organic synthesis for creating various functionalized molecules.

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