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

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5:19 minutes

Problem 74a

Textbook Question

Rank the following species in each set from best nucleophile to poorest nucleophile.
a.

Verified step by step guidance

Step 1: Understand the concept of nucleophilicity. Nucleophilicity refers to the ability of a species to donate a pair of electrons to an electrophile. Factors affecting nucleophilicity include charge, electronegativity, steric hindrance, and solvent effects.

Step 2: Analyze the charge of each species. Generally, negatively charged species are better nucleophiles than their neutral counterparts because they have a higher electron density available for donation.

Step 3: Consider electronegativity. Species with lower electronegativity are better nucleophiles because they hold onto their electrons less tightly, making them more available for bonding.

Step 4: Evaluate steric hindrance. Bulky groups around the nucleophilic center can hinder its ability to approach the electrophile, reducing nucleophilicity.

Step 5: Account for solvent effects. In polar protic solvents, nucleophilicity decreases for smaller ions due to hydrogen bonding, while in polar aprotic solvents, nucleophilicity is less affected by hydrogen bonding and depends more on charge and electronegativity.

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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 species to donate an electron pair to an electrophile during a chemical reaction. It is influenced by factors such as charge, electronegativity, and steric hindrance. Generally, negatively charged species are better nucleophiles than neutral ones, and less electronegative atoms are more nucleophilic due to their willingness to share electrons.

Solvent Effects

The solvent can significantly impact nucleophilicity. In polar protic solvents, nucleophiles are often stabilized by solvation, which can hinder their reactivity. Conversely, in polar aprotic solvents, nucleophiles are less solvated and can exhibit greater reactivity, making the choice of solvent crucial when ranking nucleophiles.

Steric Hindrance

Steric hindrance refers to the crowding around a reactive site that can impede the approach of a nucleophile to an electrophile. Bulky groups attached to a nucleophile can reduce its ability to effectively collide with and react with an electrophile, thus affecting its nucleophilicity. Smaller, less hindered nucleophiles are generally more effective in nucleophilic attacks.

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