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

Ranking Acidity

Organic Chemistry

3. Acids and Bases

Ranking Acidity

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4:20 minutes

Problem 44c

Textbook Question

Without using pK_a values, pick out the least reactive (most stable) base in each pair. Explain your answer.
(c)

Verified step by step guidance

Step 1: Understand the concept of base stability. A base's stability is influenced by factors such as resonance, electronegativity, inductive effects, and steric hindrance. The more stable a base, the less reactive it is.

Step 2: Examine resonance effects. If a base can delocalize its negative charge through resonance, it will be more stable. Compare the structures in the pair to see if one has resonance stabilization.

Step 3: Consider electronegativity. A base with its negative charge on a more electronegative atom will be more stable. Check the atoms bearing the negative charge in each base of the pair.

Step 4: Evaluate inductive effects. Electron-withdrawing groups near the negatively charged atom can stabilize the base by pulling electron density away. Look for such groups in the structures.

Step 5: Assess steric hindrance. A base with bulky groups around the negatively charged atom may be less stable due to steric repulsion. Compare the steric environments of the bases in the pair.

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Key Concepts

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

Acidity and Basicity

Acidity refers to the tendency of a substance to donate protons (H⁺), while basicity is the ability to accept protons. The stability of a base is often inversely related to its reactivity; a more stable base is less likely to react with protons. Understanding the relationship between acids and bases is crucial for determining which base is less reactive in a given pair.

Resonance Stabilization

Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, leading to a delocalization of electrons. This delocalization can enhance the stability of a base, making it less reactive. When comparing bases, those that can stabilize their negative charge through resonance are typically more stable and less reactive.

Electronegativity and Charge Distribution

Electronegativity is the tendency of an atom to attract electrons towards itself. In the context of bases, the distribution of charge and the electronegativity of atoms can influence stability. A base with a negative charge on a more electronegative atom is generally more stable, as the electronegative atom can better accommodate the negative charge, leading to decreased reactivity.

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Related Practice

Textbook Question

Identify the stronger base in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(a)

Textbook Question

Identify the stronger base in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(c)

Textbook Question

Identify the stronger acid in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(a)

Textbook Question

Without using pK_a values, pick out the least reactive (most stable) base in each pair. Explain your answer.

(a)

Textbook Question

Which of the following indicated atoms would you expect to be most basic?

(a)

Textbook Question

Without using pK_a values, pick out the more acidic compound in each pair. Explain your answer.

(a)

Textbook Question

Without using pK_a values, pick out the more reactive (least stable) base in each pair. Explain your answer.

(a)

Textbook Question

Tenormin, a member of the group of drugs known as beta-blockers, is used to treat high blood pressure and improve survival after a heart attack. It works by slowing down the heart to reduce its workload. Which atom in Tenormin is the most basic?

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Without using pKa values, pick out the least reactive (most stable) base in each pair. Explain your answer. (c)

Key Concepts

Acidity and Basicity

Resonance Stabilization

Electronegativity and Charge Distribution

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Without using pK_a values, pick out the least reactive (most stable) base in each pair. Explain your answer.
(c)