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

1:28 minutes

Problem 22b

Textbook Question

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

Verified step by step guidance

Identify the nucleophiles in the problem. A nucleophile is a species that donates a pair of electrons to form a new covalent bond. Look at the structures of the two nucleophiles provided and determine their key features, such as charge, electronegativity, and steric hindrance.

Consider the solvent type. Determine whether the solvent is polar protic (e.g., water, alcohols) or polar aprotic (e.g., acetone, DMSO). Polar protic solvents stabilize anions through hydrogen bonding, which can reduce the reactivity of negatively charged nucleophiles. Polar aprotic solvents, on the other hand, do not stabilize anions as effectively, allowing nucleophiles to remain more reactive.

Evaluate the charge and basicity of the nucleophiles. Negatively charged nucleophiles are generally more reactive than neutral ones in polar aprotic solvents. In polar protic solvents, smaller nucleophiles (e.g., F⁻) are more stabilized by hydrogen bonding, making larger nucleophiles (e.g., I⁻) more reactive.

Assess steric hindrance. Bulky nucleophiles are less reactive because their size makes it harder for them to approach the electrophile. Compare the steric bulk of the two nucleophiles to determine which one is less hindered.

Combine all the factors (solvent type, charge, basicity, and steric hindrance) to determine which nucleophile would be more reactive in the given solvent. Use this analysis to make your conclusion about the relative reactivity of the two nucleophiles.

Verified video answer for a similar problem:

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

Video duration:

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 species to donate an electron pair to an electrophile during a chemical reaction. Factors influencing nucleophilicity include charge, electronegativity, and the solvent's properties. Generally, negatively charged species are more nucleophilic than their neutral counterparts, and nucleophiles are more reactive in polar aprotic solvents due to reduced solvation.

Solvent Effects

The solvent can significantly influence the reactivity of nucleophiles. Polar protic solvents stabilize nucleophiles through hydrogen bonding, which can hinder their reactivity. In contrast, polar aprotic solvents do not solvate anions as effectively, allowing nucleophiles to remain more reactive. Understanding the solvent's role is crucial for predicting reaction outcomes.

Electrophilicity

Electrophilicity is the tendency of a species to accept an electron pair from a nucleophile. Electrophiles are typically electron-deficient species, such as carbocations or carbonyl compounds. The strength of an electrophile can affect the overall reaction rate, as a more electrophilic center will react more readily with nucleophiles, making it essential to consider both nucleophilicity and electrophilicity in reaction mechanisms.

Watch next

Master Understanding the difference between basicity and nucleophilicity. with a bite sized video explanation from Johnny

Start learning