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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3:13 minutes

Problem 10a,b

Textbook Question

Indicate whether each of the following solvents is protic or aprotic:
a. chloroform (CHCl₃)
b. diethyl ether

Verified step by step guidance

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

Step 2: Analyze chloroform (CHCl₃). Chloroform contains hydrogen atoms bonded to carbon, not to an electronegative atom like oxygen or nitrogen. Therefore, it cannot participate in hydrogen bonding and is classified as an aprotic solvent.

Step 3: Analyze diethyl ether (C₂H₅OC₂H₅). Diethyl ether has oxygen atoms, but the hydrogens in the molecule are bonded to carbon atoms, not to the oxygen. Since it cannot form hydrogen bonds, it is also classified as an aprotic solvent.

Step 4: Summarize the findings: Both chloroform and diethyl ether are aprotic solvents because neither contains hydrogen atoms bonded to electronegative atoms capable of hydrogen bonding.

Step 5: Apply this concept to other solvents by checking for the presence of hydrogen atoms bonded to electronegative atoms (protic) or their absence (aprotic).

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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 for understanding their reactivity and solvation properties. Common examples include water and alcohols.

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 so through dipole interactions rather than hydrogen bonding. Examples include acetone and dimethyl sulfoxide (DMSO), which are often used in reactions where protic solvents would interfere.

Solvent Polarity

The polarity of a solvent is determined by its molecular structure and the distribution of electrical charge. Polar solvents, which include many protic solvents, can stabilize ions and polar molecules, while nonpolar or aprotic solvents are better suited for dissolving nonpolar substances. Understanding solvent polarity is essential for predicting solubility and reactivity in organic reactions.

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