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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2:44 minutes

Problem 20c(iv,v)

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)

Verified step by step guidance

Step 1: Identify the reactants and their roles in the proton transfer. Ethanolate (CH3CH2O⁻) is a strong base due to its negatively charged oxygen atom, which has lone pairs of electrons. Acetic acid (CH3COOH) is a weak acid, capable of donating a proton (H⁺) from its hydroxyl group (-OH).

Step 2: Recognize the site of interaction. The negatively charged oxygen atom in ethanolate will act as a nucleophile and attack the hydrogen atom of the hydroxyl group (-OH) in acetic acid. This is the proton transfer step.

Step 3: Draw the arrow-pushing mechanism. Use curved arrows to show the movement of electrons: (i) A lone pair of electrons on the oxygen atom of ethanolate attacks the hydrogen atom of acetic acid, forming a bond. (ii) Simultaneously, the bond between the hydrogen and oxygen in acetic acid breaks, and the electrons move to the oxygen atom of acetic acid, creating an acetate ion (CH3COO⁻).

Step 4: Predict the products of the reaction. The proton transfer results in the formation of ethanol (CH3CH2OH) and acetate ion (CH3COO⁻). Ethanol is formed as the ethanolate gains a proton, and acetate ion is formed as acetic acid loses a proton.

Step 5: Verify the stability of the products. Ethanol is neutral and stable, while acetate ion is resonance-stabilized due to the delocalization of electrons between the two oxygen atoms in the carboxylate group. This makes the reaction thermodynamically favorable.

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Key Concepts

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

Proton Transfer Mechanism

Proton transfer mechanisms involve the movement of a proton (H+) from one molecule to another, often facilitated by the presence of a base or acid. In this case, ethanolate acts as a base, accepting a proton from acetic acid. Understanding the arrow-pushing notation is crucial, as it visually represents the flow of electrons during the reaction, indicating how bonds are formed and broken.

Acid-Base Reactions

Acid-base reactions are fundamental in organic chemistry, characterized by the transfer of protons between reactants. Acetic acid, a weak acid, donates a proton to the ethanolate ion, which is a strong base. Recognizing the strength of acids and bases helps predict the direction of the reaction and the stability of the resulting products.

Lone Pairs and Bond Formation

Lone pairs are pairs of valence electrons that are not involved in bonding and can play a significant role in chemical reactions. In the context of the given reaction, the lone pair on the ethanolate ion is used to form a bond with the proton from acetic acid. Understanding how lone pairs participate in bond formation is essential for predicting the products of reactions and the overall mechanism.

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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.

(c)

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,

(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)

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)

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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)

Key Concepts

Proton Transfer Mechanism

Acid-Base Reactions

Lone Pairs and Bond Formation

Watch next

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)