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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2:19 minutes

Problem 50b

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)

Verified step by step guidance

Identify the reactants: [CH3O(CH3)2]+ is a positively charged species, indicating it is electron-deficient and can act as a Lewis acid (electrophile). OH2 (water) has lone pairs of electrons, making it a Lewis base (nucleophile).

Determine the direction of electron pair movement: The lone pair on the oxygen atom of OH2 will attack the electron-deficient oxygen atom in [CH3O(CH3)2]+.

Use curved arrows to show the movement of electron pairs: Draw a curved arrow from the lone pair on the oxygen of OH2 to the oxygen atom in [CH3O(CH3)2]+, indicating the formation of a new bond.

Analyze the products: The reaction results in the formation of O(CH3)2 and [CH3OH2]+. The O(CH3)2 is neutral, and [CH3OH2]+ is a positively charged species, indicating the transfer of a proton.

Conclude the reaction mechanism: The reaction involves the transfer of a proton from the Lewis acid to the Lewis base, resulting in the formation of a new bond and the products O(CH3)2 and [CH3OH2]+.

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Key Concepts

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

Lewis Acids and Bases

Lewis acids are species that can accept an electron pair, while Lewis bases are species that can donate an electron pair. In the context of acid-base reactions, identifying which reactant acts as a Lewis acid or base is crucial for understanding the reaction mechanism and predicting the products formed.

Curved Arrows in Mechanisms

Curved arrows are used in organic chemistry to illustrate the movement of electron pairs during chemical reactions. The tail of the arrow indicates the source of the electron pair (the nucleophile), while the head points to the atom that will receive the electrons (the electrophile). This notation helps visualize the flow of electrons and the changes in bonding that occur during the reaction.

Radical Species

Radical species are atoms or molecules that contain unpaired electrons, making them highly reactive. In the provided reaction, the presence of radicals (indicated by dots) suggests that the reaction involves radical intermediates, which can significantly influence the reaction pathway and the stability of the products formed.

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Related Practice

Textbook Question

In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.

(a)

Textbook Question

Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.

(a)

(b)

Textbook Question

Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with the strong nucleophile sodium ethoxide, Na⁺ ⁻OCH₂CH₃.

b. NH₄⁺

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.

(d)

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

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

(c)

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