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

Acids and Bases

Organic Chemistry

3. Acids and Bases

Acids and Bases

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Problem 24

Textbook Question

An unknown base (B⁻) has been identified as very weak. What does this tell you about the strength of its conjugate acid, HB? Is it stable or unstable? Is it reactive or unreactive?

Verified step by step guidance

Step 1: Recall the relationship between the strength of a base and its conjugate acid. A very weak base corresponds to a very strong conjugate acid. This is because the ability of the base to accept a proton is inversely related to the ability of its conjugate acid to donate a proton.

Step 2: Analyze the stability of the conjugate acid (HB). Strong acids tend to be stable because they readily donate protons and form stable conjugate bases. Therefore, if the base (B⁻) is very weak, its conjugate acid (HB) is likely stable.

Step 3: Consider the reactivity of the conjugate acid (HB). Strong acids are highly reactive because they easily donate protons in chemical reactions. Since HB is a strong acid, it is expected to be reactive.

Step 4: Summarize the findings: A very weak base (B⁻) indicates that its conjugate acid (HB) is strong, stable, and reactive.

Step 5: Apply this concept to other acid-base pairs to understand how the strength of a base influences the properties of its conjugate acid in various chemical contexts.

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Key Concepts

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

Conjugate Acid-Base Relationship

In acid-base chemistry, a conjugate acid is formed when a base accepts a proton (H⁺). The strength of a base is inversely related to the strength of its conjugate acid; thus, if a base is very weak, its conjugate acid is likely to be strong. This relationship is fundamental in predicting the behavior of acids and bases in chemical reactions.

Stability of Conjugate Acids

The stability of a conjugate acid is influenced by its ability to stabilize the positive charge that results from protonation. A weak base typically forms a stable conjugate acid because the conjugate acid does not readily donate the proton back, indicating that it is less reactive. Stability often correlates with the presence of electronegative atoms or resonance structures that can delocalize charge.

Reactivity of Acids and Bases

Reactivity in acid-base chemistry refers to how readily an acid donates protons or a base accepts them. A weak base, such as B⁻, suggests that its conjugate acid, HB, is unreactive, as it does not easily release protons. This unreactivity is a characteristic of stable conjugate acids, which do not participate in further acid-base reactions under standard conditions.

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Related Practice

Textbook Question

Using the convention that the acid and base are on the left side of the chemical equation, label the acid, base, conjugate acid, and conjugate base in the following reactions.

(c)

Textbook Question

When an atom loses a proton in an acid–base reaction, its formal charge is decreased by one. Thinking about the equation for calculating formal charge, explain this observation in your own words.