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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3:01 minutes

Problem 16

Textbook Question

Suggest an arrow-pushing mechanism for the following reaction. Is the hydroxyl group acting as a base, acid, Lewis base, or Lewis acid?

Verified step by step guidance

Step 1: Begin by identifying the reactants and products in the reaction. Look for changes in bonding, functional groups, or charge distribution to determine the key transformations occurring.

Step 2: Analyze the role of the hydroxyl group (-OH). Determine whether it donates a proton (acting as an acid), accepts a proton (acting as a base), donates an electron pair (acting as a Lewis base), or accepts an electron pair (acting as a Lewis acid).

Step 3: Draw the initial structure of the reactants and use curved arrows to show the movement of electrons. For example, if the hydroxyl group is donating a proton, show the bond between the oxygen and hydrogen breaking, with the electrons moving toward the oxygen atom.

Step 4: Continue the arrow-pushing mechanism to show how the electrons rearrange to form the products. Ensure that all charges and lone pairs are accounted for in the intermediate and final structures.

Step 5: Summarize the role of the hydroxyl group based on the mechanism. If it donates a proton, it acts as an acid; if it accepts a proton, it acts as a base; if it donates an electron pair, it acts as a Lewis base; if it accepts an electron pair, it acts as a Lewis acid.

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Key Concepts

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

Arrow-Pushing Mechanism

Arrow-pushing mechanisms are diagrams used in organic chemistry to illustrate the movement of electrons during chemical reactions. They show how bonds are formed and broken, indicating the flow of electron density with arrows. Understanding these mechanisms is crucial for predicting the outcome of reactions and identifying reactive intermediates.

Acid-Base Theory

Acid-base theory in organic chemistry defines acids as proton donors and bases as proton acceptors. This concept helps in understanding the role of functional groups in reactions. For instance, a hydroxyl group (-OH) can act as an acid by donating a proton or as a base by accepting one, depending on the reaction context.

Lewis Acids and Bases

Lewis acid-base theory expands the definition of acids and bases beyond protons to include electron pair acceptors (Lewis acids) and electron pair donors (Lewis bases). This concept is essential for analyzing reactions where electron transfer occurs, such as in nucleophilic substitutions or additions, and helps determine the role of various functional groups in a reaction.

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Related Practice

Textbook Question

Provide a reasonable arrow-pushing mechanism for the following Lewis acid–Lewis base reactions.

(b)

Textbook Question

For the following acid–base reaction, (a) identify the acid and conjugate acid

Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH₂.

(d) Carbenes are also Lewis bases. Based on your answers to (a) and (b), explain this observation.

Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH₂.

Textbook Question

What is the major product of the following reactions?

Textbook Question

Specify which in each pair is the harder Lewis base. Justify your choice beyond just looking at Table 20.2.

(b)

Textbook Question

Specify which in each pair is the harder Lewis acid. Justify your choice beyond just looking at Table 20.2.

(a) Al³⁺ vs. B³⁺

Textbook Question

Suggest an arrow-pushing mechanism for each of the following acid–base reactions.

(d) [an intramolecular reaction]

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