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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4:08 minutes

Problem 3

Textbook Question

Rank the reactivity of the following anions with a general electrophile from least to most reactive.

Verified step by step guidance

Step 1: Understand the concept of nucleophilicity. Nucleophilicity refers to the ability of a species (anion in this case) to donate a pair of electrons to an electrophile. Factors such as charge, electronegativity, steric hindrance, and resonance stabilization influence nucleophilicity.

Step 2: Analyze the charge of each anion. Anions with a higher negative charge density are generally more nucleophilic because they have a stronger tendency to donate electrons.

Step 3: Consider electronegativity. Anions derived from less electronegative atoms are typically more nucleophilic because they hold their electrons less tightly, making them more available for donation.

Step 4: Evaluate steric hindrance. Bulky anions with large substituents may have reduced nucleophilicity due to difficulty in approaching the electrophile.

Step 5: Assess resonance stabilization. Anions that are resonance-stabilized are less reactive because their negative charge is delocalized, making them less available to interact with the electrophile.

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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, forming a new bond. Anions, which are negatively charged, typically exhibit higher nucleophilicity due to their excess electrons. Factors influencing nucleophilicity include charge, electronegativity, and solvent effects, with stronger bases generally being more nucleophilic.

Electrophiles

Electrophiles are species that accept electron pairs from nucleophiles during chemical reactions. They are usually positively charged or neutral molecules with an electron-deficient atom. Understanding the nature of electrophiles is crucial, as their reactivity can vary based on their structure and the presence of electron-withdrawing or donating groups.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants transform into products, including the movement of electrons. Analyzing mechanisms helps predict the reactivity of anions with electrophiles, as it reveals the intermediates and transition states involved. Knowledge of common mechanisms, such as nucleophilic substitution or addition, is essential for ranking reactivity.

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