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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2:05 minutes

Problem 1d

Textbook Question

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

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. Stronger nucleophiles are typically more negatively charged, less sterically hindered, and less stabilized by resonance or electronegative atoms.

Step 2: Analyze the chemical structures provided. Formic acid (a) has a neutral hydroxyl group (-OH) attached to the carbonyl carbon, while formate (b) is the conjugate base of formic acid and carries a negative charge on the oxygen atom.

Step 3: Consider the role of charge. Negatively charged species, like formate (b), are generally stronger nucleophiles than their neutral counterparts because the negative charge increases their electron density, making them more reactive.

Step 4: Evaluate resonance stabilization. Formate (b) has resonance structures that delocalize the negative charge, but it still retains a higher electron density compared to the neutral formic acid (a), making it a stronger nucleophile.

Step 5: Conclude that formate (b) is the stronger nucleophile compared to formic acid (a) due to its negative charge and higher electron density.

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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 negatively charged or have lone pairs of electrons that can be readily donated. In this context, comparing formic acid and formate involves assessing their ability to act as nucleophiles based on their structure and charge.

Acid-Base Chemistry

Understanding acid-base chemistry is crucial for determining nucleophilicity. Formic acid (a weak acid) can donate a proton (H+) to form the formate ion, which is its conjugate base. The presence of a negative charge on formate enhances its nucleophilicity compared to the neutral formic acid, making it a stronger nucleophile in reactions.

Resonance Stabilization

Resonance stabilization plays a significant role in the reactivity of nucleophiles. The formate ion can delocalize its negative charge over the oxygen atoms, which stabilizes the ion and enhances its nucleophilic character. In contrast, formic acid lacks this resonance stabilization for nucleophilic attack, making formate the stronger nucleophile in this comparison.

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