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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1:36 minutes

Problem 53e

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

Verified step by step guidance

Identify the nucleophilic site in the compound CH3CH2OH. The oxygen atom in the hydroxyl group (-OH) has lone pairs of electrons, making it a potential nucleophilic site.

Recognize the electrophile in the reaction, which is BF3. Boron trifluoride (BF3) is a strong electrophile due to the electron deficiency of the boron atom, which has an incomplete octet.

Use a curved arrow to represent the movement of electrons from the nucleophile to the electrophile. Draw a curved arrow starting from one of the lone pairs on the oxygen atom of CH3CH2OH and pointing towards the boron atom in BF3.

Understand that the interaction between the nucleophile and the electrophile will result in the formation of a coordinate covalent bond. The lone pair of electrons from the oxygen will be shared with the boron atom, completing its octet.

Consider the resulting complex, where the oxygen atom is now bonded to the boron atom, forming an adduct. This interaction stabilizes the electron-deficient boron by sharing the lone pair from the oxygen.

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Key Concepts

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

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in reaction mechanisms. They are typically rich in electrons and can be negatively charged ions or neutral molecules with lone pairs. In the context of the question, CH3CH2OH acts as a nucleophile due to the lone pairs on the oxygen atom.

Electrophiles

Electrophiles are species that accept an electron pair to form a chemical bond. They are electron-deficient and often have a positive charge or a partial positive charge. In this question, BF3 is the electrophile, as it has an empty p-orbital on the boron atom, making it electron-deficient and capable of accepting electrons from a nucleophile.

Curved Arrow Notation

Curved arrow notation is used in organic chemistry to depict the movement of electron pairs during chemical reactions. The tail of the arrow starts at the electron source (nucleophile) and points towards the electron sink (electrophile). In this reaction, arrows would show the lone pair on the oxygen of CH3CH2OH moving towards the boron atom in BF3, indicating the formation of a new bond.

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Related Practice

Textbook Question

Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.

Textbook Question

Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.

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.

(f) (CH₃)₂S

Textbook Question

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

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)

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