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

22. Carboxylic Acid Derivatives: NAS

Carboxylation

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylation

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Multiple Choice

Determine the major product for the following reaction.

Cyclopentanol with a hydroxyl group attached to a carbon atom.

Cyclopentanol with a hydroxyl group on a different carbon atom.

Cyclopentanol with a carbonyl and hydroxyl group attached.

Cyclopentanol with a carbonyl group and a hydroxyl group on adjacent carbons.

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Verified step by step guidance

Identify the starting material as cyclopentane, a five-membered carbon ring.

The first step involves the reaction of cyclopentane with bromine (Br2) under light (hv), which is a radical halogenation process. This will substitute a hydrogen atom on the cyclopentane ring with a bromine atom, forming bromocyclopentane.

In the second step, bromocyclopentane is treated with magnesium in ether, forming a Grignard reagent. The bromine atom is replaced by a magnesium bromide group, resulting in cyclopentylmagnesium bromide.

The third step involves the reaction of the Grignard reagent with carbon dioxide (CO2). The nucleophilic carbon in the Grignard reagent attacks the electrophilic carbon in CO2, forming a carboxylate intermediate.

Finally, the carboxylate intermediate is protonated during the H3O+ workup, resulting in the formation of cyclopentane carboxylic acid as the major product.