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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Problem 52

Textbook Question

Which atoms in the enol ether would you expect to react with Br⁺ ?

Verified step by step guidance

Step 1: Analyze the structure of the enol ether. The enol ether contains a double bond between the two carbon atoms (C=C) and an oxygen atom bonded to one of the carbons. The oxygen atom has lone pairs of electrons, making it nucleophilic.

Step 2: Understand the reactivity of Br⁺. Bromine in its Br⁺ form is electrophilic, meaning it seeks out regions of high electron density to react with.

Step 3: Identify the regions of high electron density in the enol ether. The double bond (C=C) is electron-rich due to the π-electrons, and the oxygen atom is electron-rich due to its lone pairs.

Step 4: Predict the interaction. Br⁺ is likely to react with the π-electrons of the double bond (C=C) or the lone pairs on the oxygen atom. These are the two nucleophilic sites in the molecule.

Step 5: Consider the most likely site of attack. The double bond (C=C) is typically more reactive toward electrophiles like Br⁺ because the π-electrons are more accessible compared to the lone pairs on oxygen. However, the oxygen atom may also participate depending on the reaction conditions.

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Key Concepts

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

Enol Ethers

Enol ethers are compounds that contain a carbon-carbon double bond (alkene) adjacent to an ether functional group (R-O-R'). They are characterized by the presence of a hydroxyl group (OH) and a carbonyl group (C=O) in their tautomeric forms. Understanding the structure of enol ethers is crucial for predicting their reactivity, particularly in electrophilic addition reactions.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, resulting in the formation of a new bond. In the context of the enol ether, the Br⁺ ion acts as an electrophile that can react with the nucleophilic sites in the molecule, such as the double bond or the oxygen atom, leading to the formation of a brominated product.

Nucleophilicity of Oxygen

Oxygen in enol ethers can exhibit nucleophilic behavior due to its lone pairs of electrons. This property allows it to interact with electrophiles like Br⁺. The nucleophilicity of oxygen is significant in determining which atoms in the enol ether will react with the electrophile, influencing the overall reaction pathway and product formation.

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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.

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.

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.

(e) CH₃CH₂OH

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.

(f) (CH₃)₂S

Textbook Question

To which atom of formaldehyde would you expect H⁺ to add?

Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(b)

Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction