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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1:50 minutes

Problem 18d

Textbook Question

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

Verified step by step guidance

Step 1: Identify the acid and base in the reaction. The molecule with the hydroxyl group (-OH) attached to the carbonyl group is the acid, as it can donate a proton. The molecule with the amine group (-NH2) is the base, as it can accept a proton.

Step 2: Draw the initial interaction. The lone pair of electrons on the nitrogen atom of the amine group will attack the hydrogen atom of the hydroxyl group on the acid. This is the proton transfer step.

Step 3: Represent the movement of electrons using curved arrows. The curved arrow starts from the lone pair on the nitrogen and points toward the hydrogen atom of the hydroxyl group. Simultaneously, another curved arrow shows the breaking of the O-H bond, with the electrons moving to the oxygen atom.

Step 4: Show the resulting products. After the proton transfer, the amine group becomes protonated, forming an ammonium ion (-NH3+). The acid loses a proton, forming its conjugate base, which is the deprotonated carboxylate ion (-COO−).

Step 5: Verify the equilibrium. The reaction is reversible, as indicated by the double arrow. Ensure that the products (ammonium ion and carboxylate ion) are correctly drawn and match the structures provided in the image.

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Key Concepts

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

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, acids are proton donors, while bases are proton acceptors. Understanding the strength of acids and bases, as well as their conjugate pairs, is crucial for predicting the direction of the reaction and the stability of the resulting species.

Arrow-Pushing Mechanism

The arrow-pushing mechanism is a method used to illustrate the movement of electrons during chemical reactions. Arrows indicate the flow of electron pairs, showing how bonds are formed and broken. This visual representation helps in understanding the stepwise progression of reactions, particularly in acid-base chemistry where proton transfers are involved.

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 charged intermediates, influencing the reaction pathway and the stability of products. Recognizing resonance can help predict the most favorable reaction mechanisms and the stability of the resulting species.

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Related Practice

Textbook Question

What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]

(a)