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

8. Elimination Reactions

Solvents

Organic Chemistry

8. Elimination Reactions

Solvents

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2:40 minutes

Problem 10c,d

Textbook Question

Indicate whether each of the following solvents is protic or aprotic:
c. acetic acid
d. hexane

Verified step by step guidance

Step 1: Understand the difference between protic and aprotic solvents. Protic solvents have hydrogen atoms bound to electronegative atoms (like oxygen or nitrogen) that can participate in hydrogen bonding. Aprotic solvents lack such hydrogen atoms and cannot form hydrogen bonds.

Step 2: Analyze acetic acid (CH₃COOH). Acetic acid contains a hydroxyl (-OH) group attached to a carbonyl group. The hydrogen in the hydroxyl group is bound to oxygen, an electronegative atom, making acetic acid a protic solvent.

Step 3: Analyze hexane (C₆H₁₄). Hexane is a hydrocarbon composed entirely of carbon and hydrogen atoms. It does not contain any electronegative atoms like oxygen or nitrogen, nor does it have hydrogen atoms capable of forming hydrogen bonds. Therefore, hexane is an aprotic solvent.

Step 4: Summarize the findings: Acetic acid is a protic solvent because it has a hydroxyl group capable of hydrogen bonding. Hexane is an aprotic solvent because it lacks electronegative atoms and hydrogen bonding capability.

Step 5: Apply this understanding to other solvents in future problems by identifying functional groups and determining whether hydrogen bonding is possible.

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Key Concepts

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

Protic Solvents

Protic solvents are those that have a hydrogen atom attached to an electronegative atom, typically oxygen or nitrogen, allowing them to form hydrogen bonds. This characteristic enables protic solvents to donate protons (H+) in chemical reactions, which is crucial in many organic reactions, particularly those involving nucleophiles and electrophiles.

Aprotic Solvents

Aprotic solvents lack hydrogen atoms bonded to electronegative atoms, meaning they cannot donate protons. These solvents can still solvate ions and molecules but do not participate in hydrogen bonding. Aprotic solvents are often used in reactions where strong nucleophiles are required, as they do not hinder nucleophilic attack.

Solvent Properties in Organic Chemistry

The choice of solvent in organic chemistry significantly affects reaction mechanisms and outcomes. Protic and aprotic solvents influence the solubility of reactants, the stability of intermediates, and the overall reaction rate. Understanding the properties of solvents helps chemists select the appropriate medium for specific reactions, optimizing yields and selectivity.

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