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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3:07 minutes

Problem 57b

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.
b.

Verified step by step guidance

Step 1: Identify the electrophile and nucleophile in the reaction. The electrophile is the H atom in H-Br because it is electron-deficient and can accept electrons. The nucleophile is the π-electrons in the double bond of CH3CH=CH2 because they are electron-rich and can donate electrons.

Step 2: Analyze the bond-breaking process. The bond between H and Br in H-Br breaks heterolytically, meaning the electrons from the bond move entirely to Br, forming Br⁻. Represent this with a curved arrow starting from the bond between H and Br and pointing toward Br.

Step 3: Analyze the bond-making process. The π-electrons in the double bond of CH3CH=CH2 attack the H atom from H-Br, forming a new bond between the H atom and one of the carbons in the double bond. Represent this with a curved arrow starting from the π-electrons in the double bond and pointing toward the H atom.

Step 4: Determine the intermediate formed. After the bond-making and bond-breaking processes, a carbocation intermediate is formed. The carbon that does not bond with the H atom becomes positively charged (CH3CH-CH3⁺).

Step 5: Draw the curved arrows and intermediates clearly. Ensure the curved arrows illustrate the movement of electrons during the bond-making and bond-breaking processes, and show the formation of Br⁻ and the carbocation intermediate CH3CH-CH3⁺.

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Key Concepts

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

Electrophiles

Electrophiles are species that accept electrons during a chemical reaction. They are typically positively charged or neutral molecules with an electron-deficient atom, making them attractive to nucleophiles. In organic reactions, common electrophiles include carbocations, carbonyl compounds, and halogens. Understanding the nature of electrophiles is crucial for predicting reaction pathways and mechanisms.

Nucleophiles

Nucleophiles are electron-rich species that donate electrons to electrophiles during a reaction. They can be negatively charged ions or neutral molecules with lone pairs of electrons. Common examples include hydroxide ions, alkoxides, and amines. Recognizing nucleophiles is essential for understanding how they interact with electrophiles to form new bonds in organic reactions.

Curved Arrows in Mechanisms

Curved arrows are used in organic chemistry to represent the movement of electrons during chemical reactions. A curved arrow starts at the source of electron density (like a nucleophile) and points to the destination (like an electrophile), indicating bond formation or breaking. This notation helps visualize reaction mechanisms and is vital for illustrating how reactants transform into products.

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Related Practice

Textbook Question

The following reaction steps are shown using conventional electron pushing. (a) Draw the second product whose formation would have been rationalized with this same arrow.

(a)

Textbook Question

The following reaction steps are shown using conventional electron pushing. (b) Use the bouncing arrow formalism to illustrate the formation of only the product shown.

(a)

Textbook Question

For the following acid–base pairs, (v) show a mechanism for the reaction;

(e)

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.

(e) CH₃CH₂OH

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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.b.

Key Concepts

Electrophiles

Nucleophiles

Curved Arrows in Mechanisms

Watch next

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.
b.