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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3:55 minutes

Problem 21b

Textbook Question

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

Verified step by step guidance

Understand the concept of deprotonation: Deprotonation is the removal of a proton (H⁺) from a molecule, which in this case is a hydroxyl group (OH). The ability of a base to deprotonate a hydroxyl group depends on its strength.

Identify the hydroxyl group: The hydroxyl group is represented as OH. It is a common functional group in organic chemistry, consisting of an oxygen atom bonded to a hydrogen atom.

Consider the strength of the base: Sodium hydroxide (NaOH) is a strong base. Strong bases are more likely to deprotonate weak acids, such as alcohols, which contain hydroxyl groups.

Evaluate the acidity of the hydroxyl group: Hydroxyl groups in alcohols are weakly acidic. The pKa of a typical alcohol is around 16-18, indicating that it can be deprotonated by a strong base.

Conclude the likelihood of deprotonation: Given that NaOH is a strong base, it can favorably deprotonate a hydroxyl group by removing the hydrogen ion (H⁺), forming water (H₂O) and the corresponding alkoxide ion.

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Key Concepts

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

Acid-Base Chemistry

Acid-base chemistry involves the transfer of protons between molecules. A base is a substance that can accept protons, while an acid can donate them. Understanding the strength of acids and bases is crucial for predicting reactions, such as deprotonation, where a base removes a proton from an acid.

pKa and Basicity

The pKa value of a compound indicates its acidity; lower pKa values mean stronger acids. A base can deprotonate an acid if the base's conjugate acid has a higher pKa than the acid being deprotonated. NaOH is a strong base, capable of deprotonating hydroxyl groups due to its high basicity.

Hydroxyl Group

A hydroxyl group consists of an oxygen atom bonded to a hydrogen atom (-OH). It is a common functional group in organic chemistry, found in alcohols. The ability of a base to deprotonate a hydroxyl group depends on the base's strength and the acidity of the hydroxyl group.