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 8a

Textbook Question

Sulfuric acid is a very strong acid. Show how the following equation can be used to explain that sulfuric acid is at once an Arrhenius, Brønsted–Lowry, and Lewis acid.

Verified step by step guidance

Step 1: Analyze the chemical equation provided. Sulfuric acid (H₂SO₄) reacts with water (H₂O) to produce hydronium ion (H₃O⁺) and bisulfate ion (HSO₄⁻). This reaction demonstrates the acid dissociation process.

Step 2: Explain sulfuric acid as an Arrhenius acid. According to Arrhenius theory, an acid increases the concentration of H⁺ ions in aqueous solution. In this reaction, sulfuric acid donates a proton (H⁺) to water, forming H₃O⁺, which increases the H⁺ concentration in the solution.

Step 3: Explain sulfuric acid as a Brønsted–Lowry acid. According to Brønsted–Lowry theory, an acid is a proton donor. Sulfuric acid donates a proton (H⁺) to water, which acts as a Brønsted–Lowry base by accepting the proton, forming H₃O⁺.

Step 4: Explain sulfuric acid as a Lewis acid. According to Lewis theory, an acid is an electron pair acceptor. In this reaction, sulfuric acid accepts an electron pair from water during the formation of the hydronium ion (H₃O⁺), demonstrating its role as a Lewis acid.

Step 5: Summarize the versatility of sulfuric acid. The reaction shows that sulfuric acid fulfills the criteria for being an Arrhenius acid (increases H⁺ concentration), a Brønsted–Lowry acid (proton donor), and a Lewis acid (electron pair acceptor), highlighting its strong acidic nature.

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Key Concepts

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

Arrhenius Acid

An Arrhenius acid is defined as a substance that increases the concentration of hydrogen ions (H⁺) in aqueous solution. In the case of sulfuric acid (H₂SO₄), it dissociates in water to produce H₃O⁺ ions, demonstrating its role as an Arrhenius acid. This definition emphasizes the acid's ability to release protons when dissolved in water.

Brønsted–Lowry Acid

According to the Brønsted–Lowry theory, an acid is a proton donor. Sulfuric acid donates a proton (H⁺) to water, forming hydronium ions (H₃O⁺) and bisulfate ions (HSO₄⁻). This interaction illustrates sulfuric acid's behavior as a Brønsted–Lowry acid, highlighting its role in proton transfer reactions.

Lewis Acid

A Lewis acid is defined as an electron pair acceptor. In the context of sulfuric acid, it can act as a Lewis acid by accepting an electron pair from a base during chemical reactions. This property allows sulfuric acid to participate in various reactions beyond simple proton donation, showcasing its versatility as a Lewis acid.

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Related Practice

Textbook Question

Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(a) Show how you would use acid–base extraction to purify the pentanal.

(b) Which of the expected impurities cannot be removed from pentanal by acid–base extractions? How would you remove this impurity?

Textbook Question

The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.

Textbook Question

The following compounds can all react as bases.

a. For each compound, show its conjugate acid. Show any resonance forms if applicable.

Textbook Question

Predict the products of the following acid–base reactions.

(g) HCOOH + CH₃O^– ⇌

(h) ⁺NH₃CH₂COOH + 2 ^–OH ⇌

Multiple Choice

Which of the following factors does not affect the acidity of a compound?

Multiple Choice

Which of the following is a characteristic of a strong acid in aqueous solution?

Multiple Choice