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 21d

Textbook Question

Which of the following bases would favorably deprotonate a hydroxyl group?
(d) Et₃N

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 and the stability of the resulting anion.

Consider the acidity of the hydroxyl group: Hydroxyl groups are generally weak acids, meaning they do not easily lose their proton. Therefore, a strong base is typically required to deprotonate them.

Evaluate the base in question: Triethylamine (Et₃N) is a tertiary amine. Amines are generally considered weak bases compared to other stronger bases like alkoxides or hydroxides.

Compare the base strength: To determine if Et₃N can deprotonate a hydroxyl group, compare its basicity to that of other bases. Strong bases like sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu) are more likely to deprotonate hydroxyl groups.

Consider steric effects: Triethylamine is a bulky base due to its three ethyl groups, which can hinder its ability to approach and deprotonate the hydroxyl group effectively. This steric hindrance can reduce its effectiveness as a base in deprotonation reactions.

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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 (H⁺) between molecules. A base is a substance that can accept a proton, while an acid is a substance that can donate a proton. Understanding the strength of acids and bases, often measured by pKa values, is crucial for predicting the outcome of deprotonation reactions.

pKa and Deprotonation

The pKa value of a compound indicates its acidity; lower pKa values correspond to stronger acids. Deprotonation occurs when a base removes a proton from an acid. For a base to deprotonate a hydroxyl group effectively, it must be strong enough to overcome the acid's pKa, meaning the base should have a higher affinity for the proton than the hydroxyl group does.

Steric and Electronic Effects

Steric and electronic effects influence a base's ability to deprotonate an acid. Steric hindrance can impede a base's approach to the proton, while electronic effects, such as the presence of electron-donating or withdrawing groups, can stabilize or destabilize the base or the conjugate acid. In the case of triethylamine (Et₃N), steric hindrance from the ethyl groups can affect its basicity and ability to deprotonate a hydroxyl group.

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