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

Previous problemNext problem

Struggling with Organic Chemistry?

Join thousands of students who trust us to help them ace their exams!Watch the first video

Multiple Choice

Why does an aprotic solvent increase the rate of an S_N2 reaction?

An aprotic solvent solvates both the cation and the anion of the nucleophile. This spreads out the electron density around the nucleophile and makes the nucleophile less nucleophilic.

An aprotic solvent solvates the cation, but not the anion, of the nucleophile. This increases the electron density around the nucleophile and makes the nucleophile more nucleophilic.

It doesn't. An aprotic solvent increases the rate of an S_N1 reaction.

An aprotic solvent solvates the anion, but not the cation, of the nucleophile. This shifts the electron density to the cation, leading to a faster reaction.

Previous problemNext problem

Verified step by step guidance

Understand the mechanism of an SN2 reaction: SN2 reactions involve a single concerted step where the nucleophile attacks the electrophile, leading to the displacement of a leaving group. The rate of this reaction is dependent on the concentration of both the nucleophile and the electrophile.

Recognize the role of solvents in SN2 reactions: Solvents can influence the nucleophilicity of the nucleophile. In SN2 reactions, the nucleophile must be strong to effectively attack the electrophile.

Differentiate between protic and aprotic solvents: Protic solvents have hydrogen atoms bonded to electronegative atoms, which can form hydrogen bonds with nucleophiles, potentially hindering their reactivity. Aprotic solvents lack these hydrogen bonds, allowing nucleophiles to remain more reactive.

Analyze the effect of aprotic solvents on nucleophiles: Aprotic solvents solvate the cation associated with the nucleophile but do not solvate the anion. This lack of solvation around the anion increases its electron density, enhancing its nucleophilicity and thus increasing the rate of SN2 reactions.

Conclude why aprotic solvents favor SN2 reactions: By increasing the nucleophilicity of the nucleophile through selective solvation, aprotic solvents facilitate the nucleophilic attack on the electrophile, thereby accelerating the SN2 reaction.