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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4:30 minutes

Problem 18a

Textbook Question

For each pair, choose the more reactive 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. It is influenced by factors such as charge, electronegativity, solvent effects, and steric hindrance.

Step 2: Analyze the first nucleophile in the pair. Consider its charge (negative charges generally increase nucleophilicity), electronegativity (lower electronegativity increases nucleophilicity), and size (larger atoms are more polarizable and often better nucleophiles in polar protic solvents).

Step 3: Analyze the second nucleophile in the pair using the same criteria as in Step 2. Compare its charge, electronegativity, and size to the first nucleophile.

Step 4: Consider the solvent type. In polar protic solvents, larger and more polarizable nucleophiles are more reactive, while in polar aprotic solvents, smaller and less electronegative nucleophiles are more reactive.

Step 5: Compare the two nucleophiles based on the above factors and determine which one is more reactive. Remember that the more reactive nucleophile will have a greater tendency to donate its electron pair to an 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 during a chemical reaction. It is influenced by factors such as charge, electronegativity, and steric hindrance. Generally, negatively charged species are more nucleophilic than their neutral counterparts, and less sterically hindered nucleophiles are more reactive.

Solvent Effects

The solvent can significantly affect 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 increased reactivity, making the choice of solvent crucial in determining which nucleophile is more reactive.

Comparative Reactivity

When comparing nucleophiles, it is essential to consider their relative reactivity based on their structure and the reaction conditions. Factors such as the presence of electron-donating or withdrawing groups, the size of the nucleophile, and the type of reaction mechanism (e.g., SN1 or SN2) can all influence which nucleophile is more reactive in a given scenario.

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Textbook Question

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

Textbook Question

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

Textbook Question

Which nucleophile would be more reactive in the solvent given?

(a)

Textbook Question

Which nucleophile would be more reactive in the solvent given?

(b)

Textbook Question

In contrast to the results of Assessment 13.18, when a secondary haloalkane is treated with sodium ethanethiolate, we predict formation of a thioether. How is this rationalized?

Textbook Question

Between pyrrole and pyrrolidine, which nitrogen would be most nucleophilic? Why?

Textbook Question

The zwitterionic form of carbonyls is often used to explain their electrophilicity. Draw the zwitterionic structure of NO⁺₂. Why is this such a great electrophile at the central nitrogen?

Textbook Question

Would you expect the following bases to favor E1 or E2 elimination?

(c)

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