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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2:50 minutes

Problem 50a

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)

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Identify the reactants: CH3O- (methoxide ion) and CH3Cl (methyl chloride).

Determine the role of each reactant: CH3O- is a Lewis base (nucleophile) because it donates an electron pair, and CH3Cl is a Lewis acid (electrophile) because it accepts an electron pair.

Use curved arrows to show the movement of electron pairs: Draw a curved arrow from the lone pair on the oxygen of CH3O- to the carbon atom in CH3Cl, indicating the formation of a new bond.

Recognize the leaving group: The Cl atom in CH3Cl will leave as Cl-, taking the electron pair from the C-Cl bond.

Write the products: The reaction forms CH3OCH3 (dimethyl ether) and Cl- (chloride ion).

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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 defined as electron pair acceptors, while Lewis bases are electron pair donors. In the context of acid-base reactions, identifying which species acts as a Lewis acid or base is crucial for understanding the reaction mechanism. For example, in the provided reaction, the negatively charged methoxide ion (CH3O⁻) acts as a Lewis base, donating an electron pair, while the methyl chloride (CH3Cl) acts as a Lewis acid, accepting the electron pair.

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, while the head points to the atom that will receive the electrons. This notation helps visualize the flow of electrons, which is essential for understanding reaction mechanisms, such as the nucleophilic attack of the methoxide ion on the electrophilic carbon of methyl chloride.

Nucleophiles and Electrophiles

Nucleophiles are species that have a high electron density and can donate an electron pair to form a bond, while electrophiles are electron-deficient species that can accept an electron pair. In the given reaction, the methoxide ion serves as a nucleophile, attacking the electrophilic carbon in methyl chloride. Recognizing these roles is fundamental for predicting the outcome of reactions and understanding the stability of intermediates formed during the process.

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Related Practice

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.

(b)

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)

Textbook Question

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

(h)

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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)

Key Concepts

Lewis Acids and Bases

Curved Arrows in Mechanisms

Nucleophiles and Electrophiles

Watch next

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)