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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5:39 minutes

Problem 20c(i,ii,iii)

Textbook Question

In the following reactions,
(i) identify the acid and base,
(ii) identify the most electron-rich atom in the base,
(iii) identify the most acidic hydrogen in the acid,
(c)

Verified step by step guidance

Step 1: Identify the acid and base in the reaction. Ethanolate (CH3CH2O⁻) is the base because it has a negative charge and can donate electrons. Acetic acid (CH3COOH) is the acid because it has a proton (H⁺) attached to the oxygen that can be donated.

Step 2: Determine the most electron-rich atom in the base. In ethanolate, the oxygen atom is the most electron-rich because it carries a negative charge and has lone pairs of electrons.

Step 3: Identify the most acidic hydrogen in the acid. In acetic acid, the hydrogen attached to the hydroxyl group (-OH) is the most acidic because it is bonded to an electronegative oxygen atom, which stabilizes the negative charge after deprotonation.

Step 4: Analyze the reaction mechanism. The base (ethanolate) will attack the acidic hydrogen of acetic acid, leading to the formation of ethanol (CH3CH2OH) and acetate ion (CH3COO⁻).

Step 5: Consider the equilibrium. The reaction is reversible, and the position of equilibrium depends on the relative acidity of acetic acid and ethanol, as well as the stability of the conjugate base (acetate ion) and conjugate acid (ethanol).

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Key Concepts

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

Acids and Bases

In organic chemistry, acids are substances that can donate a proton (H+), while bases are substances that can accept a proton. The Brønsted-Lowry theory defines acids and bases based on their ability to transfer protons. In the given reaction, acetic acid acts as the acid, and ethanolate serves as the base.

Electron-Rich Atoms

The most electron-rich atom in a base is typically the atom that has a lone pair of electrons available for bonding. In the case of ethanolate, the oxygen atom carries a negative charge and has a lone pair, making it the most electron-rich atom. This property is crucial for its ability to act as a base in the reaction.

Acidic Hydrogens

The most acidic hydrogen in an acid is the hydrogen atom that is most easily released as a proton. In acetic acid, the hydrogen attached to the hydroxyl group (-OH) is the most acidic due to the stability of the resulting acetate ion after deprotonation. Identifying this hydrogen is essential for understanding the acid's reactivity.

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Related Practice

Textbook Question

Provide an arrow-pushing mechanism for the following acid–base reactions.

(d)

Textbook Question

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

(b)

Textbook Question

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

(a)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(c)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(b)

Textbook Question

In the following reactions,

(i) identify the acid and base,

(ii) identify the most electron-rich atom in the base,

(iii) identify the most acidic hydrogen in the acid,

(b)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(a)

Textbook Question

Provide an arrow-pushing mechanism for the following hypothetical acid half-reactions. [These are only intended to help you learn about arrow pushing in acid–base reactions.]

(b)

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In the following reactions, (i) identify the acid and base, (ii) identify the most electron-rich atom in the base, (iii) identify the most acidic hydrogen in the acid, (c)

Key Concepts

Acids and Bases

Electron-Rich Atoms

Acidic Hydrogens

Watch next

In the following reactions,
(i) identify the acid and base,
(ii) identify the most electron-rich atom in the base,
(iii) identify the most acidic hydrogen in the acid,
(c)