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

3. Acids and Bases

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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2:50 minutes

Problem 1c

Textbook Question

In each case, circle the stronger nucleophile.
(c)

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. It is influenced by factors such as charge, electronegativity, steric hindrance, and solvent effects.

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

Step 3: Consider electronegativity. Less electronegative atoms are better nucleophiles because they hold onto their electrons less tightly, making them more willing to donate them.

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

Step 5: Account for solvent effects. In polar protic solvents, nucleophilicity decreases for smaller, more electronegative atoms due to hydrogen bonding. In polar aprotic solvents, nucleophilicity trends are more directly related to 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. Stronger nucleophiles are typically characterized by their high electron density and low electronegativity, which allows them to readily attack positively charged or electron-deficient centers. Factors such as charge, solvent effects, and steric hindrance also influence nucleophilicity.

Charge and Nucleophilicity

The charge of a nucleophile significantly affects its strength. Anions (negatively charged species) are generally stronger nucleophiles than their neutral counterparts because they possess an extra electron that can be donated. For example, hydroxide ion (OH-) is a stronger nucleophile than water (H2O) due to its negative charge, which enhances its electron-donating ability.

Solvent Effects

The solvent in which a reaction occurs can greatly influence nucleophilicity. Polar protic solvents can stabilize nucleophiles through hydrogen bonding, often reducing their reactivity, while polar aprotic solvents do not stabilize nucleophiles as effectively, allowing them to remain more reactive. Understanding the solvent's role is crucial for predicting the behavior of nucleophiles in various chemical environments.

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