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

Nucleophiles and Basicity

Organic Chemistry

8. Elimination Reactions

Nucleophiles and Basicity

Previous problemNext problem

Problem 22c

Textbook Question

Which nucleophile would be more reactive in the solvent given
(c)

Verified step by step guidance

Step 1: Identify the solvent given in the problem. The solvent shown in the image is tetrahydrofuran (THF), which is an aprotic solvent. Aprotic solvents do not donate hydrogen bonds and do not stabilize nucleophiles through hydrogen bonding.

Step 2: Understand the behavior of nucleophiles in aprotic solvents. In aprotic solvents, nucleophilicity is primarily determined by the basicity of the nucleophile rather than its size or polarizability. Smaller, more basic nucleophiles tend to be more reactive in aprotic solvents.

Step 3: Compare the nucleophiles provided (F⁻ and I⁻). Fluoride (F⁻) is a smaller ion and has a higher charge density compared to iodide (I⁻). This makes F⁻ a stronger base than I⁻.

Step 4: Analyze the effect of the solvent on the nucleophiles. Since THF is an aprotic solvent, it does not stabilize larger, polarizable ions like I⁻ as much as protic solvents would. Therefore, the smaller and more basic nucleophile (F⁻) will be more reactive in this solvent.

Step 5: Conclude that in the given solvent (THF), F⁻ would be the more reactive nucleophile compared to I⁻ due to its higher basicity and smaller size, which are favored in aprotic solvents.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

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

Nucleophilicity

Nucleophilicity refers to the ability of a nucleophile to donate an electron pair to an electrophile during a chemical reaction. Factors influencing nucleophilicity include charge, electronegativity, and steric hindrance. Generally, negatively charged species are more nucleophilic than neutral ones, and less sterically hindered nucleophiles are more reactive.

Solvent Effects

The solvent can significantly affect the reactivity of nucleophiles. Polar protic solvents can stabilize nucleophiles through hydrogen bonding, often reducing their reactivity, while polar aprotic solvents can enhance nucleophilicity by not stabilizing the nucleophile as much. Understanding the solvent's nature is crucial for predicting the outcome of nucleophilic reactions.

Comparative Reactivity

When comparing the reactivity of two nucleophiles, it is essential to consider their structural features and the solvent environment. Factors such as the presence of electron-donating or withdrawing groups, as well as the overall steric and electronic properties, can determine which nucleophile will be more reactive in a given reaction context.