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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2:41 minutes

Problem 21c

Textbook Question

Identify the following solvents as polar protic, polar aprotic, or nonpolar.
(c)

Verified step by step guidance

Step 1: Understand the definitions of the three types of solvents. Polar protic solvents have a hydrogen atom attached to an electronegative atom (like O or N), allowing them to form hydrogen bonds. Polar aprotic solvents are polar but lack a hydrogen atom bonded to an electronegative atom, so they cannot form hydrogen bonds. Nonpolar solvents have little to no polarity and do not dissolve ionic or polar compounds well.

Step 2: Examine the structure of the given solvent. Look for functional groups or atoms that indicate polarity (e.g., electronegative atoms like O, N, or halogens) and the presence of hydrogen atoms bonded to these electronegative atoms.

Step 3: Determine if the solvent can form hydrogen bonds. If it has a hydrogen atom bonded to an electronegative atom (e.g., -OH or -NH groups), it is polar protic. If it lacks such a hydrogen but is still polar, it is polar aprotic. If it lacks significant polarity, it is nonpolar.

Step 4: Classify the solvent based on its properties. For example, water (H₂O) is polar protic because it has -OH groups, acetone (CH₃COCH₃) is polar aprotic because it is polar but lacks -OH or -NH groups, and hexane (C₆H₁₂) is nonpolar because it is a hydrocarbon with no significant polarity.

Step 5: Apply this classification to the given solvent. Use its molecular structure and the criteria above to identify whether it is polar protic, polar aprotic, or nonpolar.

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Key Concepts

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

Polar Protic Solvents

Polar protic solvents are characterized by the presence of hydrogen atoms bonded to electronegative atoms, such as oxygen or nitrogen. These solvents can form hydrogen bonds and have a high dielectric constant, which allows them to stabilize ions. Common examples include water, alcohols, and carboxylic acids. Their ability to donate protons makes them effective in facilitating reactions involving nucleophiles.

Polar Aprotic Solvents

Polar aprotic solvents do not have hydrogen atoms bonded to electronegative atoms, which means they cannot form hydrogen bonds. However, they still possess a significant dipole moment, allowing them to dissolve ionic compounds and stabilize cations. Examples include acetone, dimethyl sulfoxide (DMSO), and acetonitrile. These solvents are often used in reactions where strong nucleophiles are involved, as they do not solvate anions as effectively as protic solvents.

Nonpolar Solvents

Nonpolar solvents are characterized by a lack of significant dipole moments, meaning they do not have regions of positive and negative charge. These solvents are typically composed of hydrocarbons and do not interact favorably with ionic or polar compounds. Common examples include hexane, benzene, and toluene. Nonpolar solvents are often used in reactions involving nonpolar reactants or in extractions where polar compounds need to be separated from nonpolar substances.

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