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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1:28 minutes

Problem 16a

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)

Verified step by step guidance

Identify the reactants and products in the given acid half-reaction. Determine which species is acting as the acid (proton donor) and which is the base (proton acceptor).

Draw the Lewis structures of all reactants to clearly visualize lone pairs and bonding electrons. This will help in understanding the electron flow.

Use curved arrows to represent the movement of electrons. Start the arrow at the electron source (e.g., a lone pair or a bond) and point it toward the electron sink (e.g., a proton or an atom that will accept the electrons).

Ensure that the proton transfer is shown correctly. For example, if a base is deprotonating the acid, draw an arrow from the lone pair on the base to the hydrogen atom of the acid, and another arrow from the bond between the hydrogen and its original atom to that atom (indicating bond breaking).

Verify that the resulting products are consistent with the acid-base reaction. Check that charges are balanced and that the electron flow adheres to the rules of organic chemistry (e.g., octet rule, formal charges).

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Key Concepts

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

Acid-Base Theory

Acid-base theory explains the behavior of acids and bases in chemical reactions. According to the Brønsted-Lowry theory, acids are proton donors while bases are proton acceptors. Understanding this concept is crucial for predicting the direction of proton transfer in reactions, which is fundamental for arrow-pushing mechanisms.

Arrow-Pushing Mechanism

Arrow-pushing mechanisms are a visual representation of the movement of electrons during chemical reactions. In these diagrams, arrows indicate the flow of electron pairs, showing how bonds are formed and broken. Mastering this technique is essential for illustrating the stepwise process of acid-base reactions and understanding the underlying electron dynamics.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In acid-base reactions, resonance can stabilize intermediates and influence the acidity or basicity of a compound. Recognizing resonance is important for predicting reaction outcomes and understanding the stability of reaction intermediates.

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Related Practice

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)

Textbook Question

Provide an arrow-pushing mechanism for the following hypothetical base half-reactions.

(c)

Textbook Question

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

(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,