Which is a better nucleophile? c. CH 3 O − or CH 3 OH in H 2 O

All right. Hi everyone. So for this question, let's go ahead and identify the stronger nuclear file in ethanol. And here we're comparing ethanolate and ethanol. So before we begin, let's recall that NU files are electron rich species that seek out and react with electron deficient species known as electro Pyles. Now, there are a few factors that determine the relative strength of a nuclear file compared to others. But regardless of the solvent that you're using, right, the charge is going to have an effect because recall that regardless of solvent negatively charged NU files are stronger than neutral ones. And the reason why I'm bringing this up right is because I'd like to focus your attention now on ethanolate and ethanol because ethanolate is an anion, right? It has a charge of minus one but ethanol is neutral, meaning it has no charge. So because of this difference alone, right? Regardless of the solvent in question, ethanolate is a stronger nuclear file than ethanol because of that charge. So therefore, right, ethanolate is stronger and there you have it right? With that being said, thank you very much for watching and I hope you found this helpful

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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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1:44 minutes

Problem 12c

Textbook Question

Which is a better nucleophile?
c. CH₃O⁻ or CH₃OH in H₂O

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: Compare the two species given in the problem: CH3O− (methoxide ion) and CH3OH (methanol). CH3O− is negatively charged, while CH3OH is neutral. A negatively charged species is generally a stronger nucleophile than its neutral counterpart because it has a higher electron density to donate.

Step 3: Consider the solvent, CH3OH (methanol), which is a polar protic solvent. Polar protic solvents can hydrogen bond with nucleophiles, stabilizing them and reducing their nucleophilicity. However, CH3O−, being negatively charged, will still be a better nucleophile than CH3OH, even in this solvent.

Step 4: Analyze the role of electronegativity. Both CH3O− and CH3OH have oxygen as the atom donating the electron pair. Since the electronegativity of oxygen is the same in both species, this factor does not affect the comparison.

Step 5: Conclude that CH3O− is the better nucleophile compared to CH3OH in CH3OH solvent, primarily due to its negative charge, which increases its electron-donating ability, despite the stabilizing effect of the polar protic solvent.

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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 chemical bond. Stronger nucleophiles are typically negatively charged or have lone pairs that can be readily donated. Factors influencing nucleophilicity include charge, electronegativity, and solvent effects, with more basic species generally being better nucleophiles.

Basicity vs. Nucleophilicity

While basicity measures a species' ability to accept protons (H+), nucleophilicity focuses on its ability to donate electron pairs. Although there is a correlation between the two, they are not identical; for example, a strong base may not always be a strong nucleophile in a given solvent. Understanding this distinction is crucial for predicting reactivity in organic reactions.

Solvent Effects

The solvent can significantly influence nucleophilicity, particularly in polar protic solvents like CH3OH (methanol). In such solvents, nucleophiles with negative charges can be stabilized by solvation, which can hinder their reactivity. Therefore, comparing nucleophiles in different solvents is essential, as the solvent can alter the relative nucleophilicity of species like CH3O− and CH3OH.

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