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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1:12 minutes

Problem 12c

Textbook Question

Identify the base from which the following conjugate acids were formed. [The most acidic proton is indicated.]
(c)

Verified step by step guidance

Identify the conjugate acid provided in the problem. A conjugate acid is formed when a base gains a proton (H⁺). Look for the structure of the conjugate acid and locate the proton that is indicated as the most acidic.

Remove the most acidic proton (H⁺) from the conjugate acid. This step involves deprotonation, which is the reverse of protonation. The removal of this proton will yield the base from which the conjugate acid was formed.

Analyze the resulting structure after deprotonation. Ensure that the charge and bonding are correctly adjusted. For example, if the proton was removed from an oxygen atom, the oxygen will now carry a negative charge (O⁻).

Determine the identity of the base. The base is the species that remains after the conjugate acid loses its proton. Compare the structure to known functional groups or molecules to name the base.

Verify your answer by considering the acid-base relationship. The conjugate acid-base pair should differ by exactly one proton. Ensure that the base you identified can accept a proton to regenerate the original conjugate acid.

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Key Concepts

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

Conjugate Acids and Bases

In acid-base chemistry, a conjugate acid is formed when a base accepts a proton (H+), while a conjugate base is what remains after an acid donates a proton. Understanding this relationship is crucial for identifying the base from which a conjugate acid is derived, as it directly relates to the proton transfer process.

Acidity and pKa

Acidity is a measure of how readily a substance donates protons in solution, often quantified by the pKa value. The lower the pKa, the stronger the acid, indicating a greater tendency to lose a proton. Recognizing the most acidic proton in a molecule helps in determining the corresponding base, as it highlights the site of proton donation.

Proton Transfer Mechanism

The proton transfer mechanism is a fundamental process in organic chemistry where protons are transferred between molecules, influencing their reactivity and stability. This mechanism is essential for understanding how conjugate acids and bases interconvert, allowing for the identification of the base from which a given conjugate acid is formed.

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Related Practice

Textbook Question

What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]

(c)

Textbook Question

What is the conjugate acid of each of the following bases? [The most basic atom is indicated.]

(d)

Textbook Question

Predict the product of the following Lewis acid–Lewis base reactions.

(c)

Textbook Question

Identify the acid from which the following conjugate bases were formed. [The most basic atom is indicated.]

(c)

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.

(a)

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.

Open 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?

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Identify the base from which the following conjugate acids were formed. [The most acidic proton is indicated.] (c)

Key Concepts

Conjugate Acids and Bases

Acidity and pKa

Proton Transfer Mechanism

Watch next

Identify the base from which the following conjugate acids were formed. [The most acidic proton is indicated.]
(c)