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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3:37 minutes

Problem 20b(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.]
(b)

Verified step by step guidance

Step 1: Identify the functional groups involved in the reaction. Ethylamide contains an amine group (-NH2) with a lone pair of electrons on nitrogen, and propan-2-ol contains a hydroxyl group (-OH) with lone pairs on oxygen.

Step 2: Recognize the proton transfer mechanism. The lone pair of electrons on the nitrogen atom in ethylamide can act as a base and accept a proton (H+) from the hydroxyl group of propan-2-ol.

Step 3: Draw the arrow-pushing mechanism. Use curved arrows to show the movement of electrons: (i) the lone pair on nitrogen attacks the hydrogen atom of the hydroxyl group, and (ii) the bond between the hydrogen and oxygen breaks, transferring the electrons to oxygen.

Step 4: Predict the intermediate species formed. After the proton transfer, ethylamide becomes protonated (forming ethylammonium ion), and propan-2-ol loses a proton, forming its conjugate base (propan-2-oxide ion).

Step 5: Verify the equilibrium. The reaction is reversible, as indicated by the double arrows, and the equilibrium will depend on the relative acidity and basicity of the species involved.

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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 lone pairs of electrons. In this context, the lone pair on the oxygen of propan-2-ol can act as a base, accepting a proton from the nitrogen of ethylamide. This process is crucial for understanding acid-base reactions and the formation of products in organic chemistry.

Lone Pairs and Nucleophilicity

Lone pairs are pairs of valence electrons that are not involved in bonding and can participate in chemical reactions. In this reaction, the lone pair on the oxygen atom of propan-2-ol makes it a nucleophile, allowing it to attack the proton on the nitrogen of ethylamide. Understanding the role of lone pairs is essential for predicting reaction pathways and products.

Reaction Products Prediction

Predicting the products of a chemical reaction involves understanding the reactants' functional groups and the mechanism of the reaction. In this case, the proton transfer will lead to the formation of a protonated ethylamide and an alkoxide ion from propan-2-ol. This prediction is based on the stability of the resulting species and the nature of the acid-base interaction.

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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.

(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,

(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,

(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)

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.]

(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.](b)

Key Concepts

Proton Transfer Mechanism

Lone Pairs and Nucleophilicity

Reaction Products Prediction

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.]
(b)