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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3:44 minutes

Problem 9c

Textbook Question

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

Verified step by step guidance

Identify the acid in the given problem and locate the most acidic proton as indicated in the question.

Recall the definition of a conjugate base: it is formed when an acid donates a proton (H⁺). This means you need to remove the most acidic proton from the acid.

Write the chemical structure of the acid and remove the indicated proton. This will result in a species with one less hydrogen atom and a negative charge on the atom that was bonded to the proton.

Ensure that the resulting conjugate base is correctly represented, including the formal charge and any resonance structures if applicable.

Double-check the structure of the conjugate base to confirm that it is consistent with the removal of the most acidic proton and that the negative charge is placed on the appropriate atom.

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Key Concepts

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

Conjugate Acid-Base Pair

A conjugate acid-base pair consists of two species that differ by the presence or absence of a proton (H+). When an acid donates a proton, it forms its conjugate base, while the base that accepts the proton becomes its conjugate acid. Understanding this relationship is crucial for identifying the conjugate base of an acid.

Acidity and pKa

Acidity refers to the tendency of a substance to donate protons, and it is quantitatively expressed by the pKa value. The lower the pKa, the stronger the acid, indicating a greater ability to lose a proton. Recognizing the most acidic proton in a molecule helps in determining which proton will be removed to form the conjugate base.

Proton Transfer Mechanism

The proton transfer mechanism is a fundamental process in acid-base chemistry where a proton is transferred from an acid to a base. This mechanism is essential for understanding how acids and bases interact in solution, and it aids in predicting the formation of conjugate bases when acids lose protons.

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Related Practice

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(f)

Textbook Question

Sodium amide (NaNH₂) dissociates to give a sodium cation (Na⁺) and amide ion (NH₂^-) a very strong base. In the following three equations, identify which definition of base is being exemplified.

(a)

Textbook Question

(c)

Textbook Question

Identify the Lewis acid and the Lewis base in each of the following reactions.

(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)