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

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Nomenclature

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Nomenclature

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Problem 21a

Textbook Question

Which of the following bases would favorably deprotonate a hydroxyl group?
(a)

Verified step by step guidance

Identify the hydroxyl group in the molecule. The hydroxyl group is characterized by an -OH functional group.

Understand the concept of deprotonation. Deprotonation involves the removal of a proton (H⁺) from the hydroxyl group, resulting in the formation of an alkoxide ion (RO⁻).

Consider the strength of the base. A strong base is required to deprotonate the hydroxyl group effectively. Organolithium compounds, such as the one shown in the image, are strong bases due to the presence of the negatively charged carbon atom.

Evaluate the ability of the base to deprotonate the hydroxyl group. The base shown in the image is an organolithium compound, which is known for its ability to deprotonate alcohols due to its high basicity.

Conclude that the organolithium compound depicted in the image is a suitable base for deprotonating a hydroxyl group, as it can effectively remove the proton from the -OH group, forming an alkoxide ion.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Deprotonation

Deprotonation is the process of removing a proton (H+) from a molecule, resulting in the formation of a conjugate base. In organic chemistry, this is often facilitated by a base, which is a substance that can accept protons. Understanding the strength and nature of the base is crucial, as stronger bases are more effective at deprotonating weak acids, such as hydroxyl groups.

Hydroxyl Group

A hydroxyl group (-OH) is a functional group consisting of an oxygen atom bonded to a hydrogen atom. It is characteristic of alcohols and phenols and can act as a weak acid, meaning it can donate a proton. The ability of a base to deprotonate a hydroxyl group depends on the stability of the resulting alkoxide ion and the strength of the base used.

Base Strength

Base strength refers to the ability of a substance to accept protons. Strong bases, such as alkoxides or hydroxides, are more effective at deprotonating hydroxyl groups compared to weak bases. The strength of a base is often determined by its position on the pKa scale, where lower pKa values indicate stronger acids and thus stronger conjugate bases.

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