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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5:25 minutes

Problem 21e

Textbook Question

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

Verified step by step guidance

Identify the pKa of the hydroxyl group. Hydroxyl groups typically have a pKa around 16-18.

Consider the concept of acid-base reactions, where a base will deprotonate an acid if the base is stronger than the conjugate base of the acid. This means the base should have a higher pKa than the hydroxyl group.

Examine the list of bases provided in the problem. Compare the pKa values of these bases to the pKa of the hydroxyl group.

Select the base with a pKa higher than that of the hydroxyl group, as it will be more likely to deprotonate the hydroxyl group.

Remember that steric hindrance and solvent effects can also influence the ability of a base to deprotonate a hydroxyl group, but the primary factor is the relative pKa values.

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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, as stronger bases are more likely to deprotonate acids, such as hydroxyl groups, by accepting their protons.

pKa and Basicity

The pKa value is a measure of the acidity of a substance, indicating how easily it can donate a proton. A lower pKa means a stronger acid. Basicity refers to a base's ability to accept protons. To deprotonate a hydroxyl group, the base must have a higher basicity than the hydroxyl's acidity, which is reflected in its pKa.

Hydroxyl Group Characteristics

A hydroxyl group consists of an oxygen atom bonded to a hydrogen atom (-OH). It is a polar group, making it capable of forming hydrogen bonds. The acidity of the hydroxyl group is relatively weak, so a base must be sufficiently strong to deprotonate it, meaning it must have a higher affinity for protons than the hydroxyl group itself.