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

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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2:49 minutes

Problem 73c

Textbook Question

Suggest an arrow-pushing mechanism for each of the following acid–base reactions
(c)

Verified step by step guidance

Identify the acid and base in the reaction. The acid is the species donating a proton (H⁺), and the base is the species accepting the proton.

Draw the Lewis structures of the acid and base to visualize the electron pairs involved in the reaction. Highlight the lone pair on the base that will interact with the proton from the acid.

Use curved arrows to represent the movement of electrons. Start the arrow at the lone pair of the base and point it toward the hydrogen atom of the acid, indicating the formation of a bond between the base and the proton.

Show the breaking of the bond between the hydrogen atom and the atom it was originally attached to in the acid. Use a curved arrow starting at the bond and pointing toward the atom that will retain the electrons after the bond breaks.

Verify the products of the reaction. The base becomes protonated, forming its conjugate acid, and the acid loses a proton, forming its conjugate base. Ensure that charges and electron counts are balanced in the final structures.

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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 acid-base reactions and the formation of conjugate acids and bases.

Arrow-Pushing Mechanism

Arrow-pushing mechanisms are a way to illustrate the movement of electrons during chemical reactions. In these diagrams, arrows represent the flow of electron pairs, indicating how bonds are formed or broken. This visual representation helps in understanding the stepwise progression of reactions, particularly in acid-base interactions.

Conjugate Acid-Base Pairs

Conjugate acid-base pairs are related species that differ by the presence of a proton. When an acid donates a proton, it forms its conjugate base, while the base that accepts the proton becomes its conjugate acid. Recognizing these pairs is essential for analyzing the equilibrium of acid-base reactions and predicting the products formed.

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Related Practice

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(b)

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(a)

Textbook Question

Identify the arrow types that are shown in each of these arrow-pushing mechanisms.

(iv)

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Only one arrow is necessary in each reaction. [Don't forget to draw in the lone pairs on this and the next two assessments.]

(a)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(h)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(c)

Textbook Question

Identify the nucleophile and the electrophile in each of the following reactions.

(b)

Textbook Question

(d)

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Suggest an arrow-pushing mechanism for each of the following acid–base reactions(c)

Key Concepts

Acid-Base Theory

Arrow-Pushing Mechanism

Conjugate Acid-Base Pairs

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Suggest an arrow-pushing mechanism for each of the following acid–base reactions
(c)