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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Tautomers of Dicarbonyl Compounds

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Tautomers of Dicarbonyl Compounds

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7:38 minutes

Problem 66a

Textbook Question

Rank these compounds in order of increasing acid strength.

Verified step by step guidance

Step 1: Analyze the molecular structures of the compounds (A, B, C, and D). Note the presence of functional groups, electronegative atoms, and resonance effects that influence acidity.

Step 2: Consider the inductive effect. Compound B contains trifluoromethyl groups (-CF3), which are highly electronegative and withdraw electron density through the inductive effect, stabilizing the conjugate base and increasing acidity.

Step 3: Evaluate resonance effects. Compound C and D have additional carbonyl groups that can participate in resonance stabilization of the conjugate base, making them more acidic than compound A.

Step 4: Compare compound A and C. Compound C has an extra carbonyl group compared to A, which increases its ability to stabilize the conjugate base through resonance, making it more acidic than A.

Step 5: Rank the compounds in order of increasing acid strength based on the combined effects of resonance and inductive stabilization: A < C < D < B.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acid Strength

Acid strength refers to the ability of a compound to donate protons (H+) in a solution. Stronger acids dissociate more completely in water, resulting in a higher concentration of H+ ions. Factors influencing acid strength include the stability of the conjugate base, electronegativity of atoms, and resonance stabilization. Understanding these factors is crucial for ranking acids.

Conjugate Base Stability

The stability of a conjugate base is a key determinant of acid strength. A more stable conjugate base corresponds to a stronger acid, as it can better accommodate the negative charge after proton donation. Factors such as electronegativity, size of the atom bearing the charge, and resonance can enhance conjugate base stability, thus influencing the acid's strength.

Resonance Effects

Resonance effects occur when a molecule can be represented by multiple valid Lewis structures, leading to delocalization of electrons. In the context of acids, resonance can stabilize the conjugate base by spreading out the negative charge over multiple atoms. This increased stability often results in a stronger acid, making resonance a critical concept in acid strength comparisons.

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