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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3:56 minutes

Problem 20c(b)

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.
(c)

Verified step by step guidance

Step 1: Analyze the starting material, which is a cyclohexene ring with a double bond. The bromine atom (:Br) is shown with a lone pair of electrons and a positive charge, indicating it is an electrophile.

Step 2: Using the bouncing arrow formalism, illustrate the interaction between the π-electrons of the double bond in cyclohexene and the electrophilic bromine atom. The π-electrons will attack the bromine atom, forming a bond between one of the carbons in the double bond and the bromine.

Step 3: As the π-electrons attack the bromine, the double bond is broken, and a carbocation is formed on the adjacent carbon. This carbocation is stabilized by the structure of the cyclohexane ring.

Step 4: The bromine atom now forms a bond with one of the carbons from the original double bond, resulting in the bromine being attached to the cyclohexane ring. The carbocation remains on the adjacent carbon.

Step 5: The product shown in the image is a bromocyclohexane with a carbocation on the adjacent carbon. Ensure the bouncing arrow formalism clearly illustrates the movement of electrons during the reaction.

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Key Concepts

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

Electron Pushing Mechanism

The electron pushing mechanism, often depicted with curved arrows, illustrates the movement of electron pairs during chemical reactions. This method helps visualize how nucleophiles attack electrophiles, leading to bond formation or breaking. Understanding this concept is crucial for predicting reaction outcomes and mechanisms in organic chemistry.

Bouncing Arrow Formalism

Bouncing arrow formalism is a specific representation used to depict the flow of electrons in a reaction, particularly in resonance structures or when showing the stabilization of charges. This method emphasizes the dynamic nature of electron movement, allowing chemists to visualize how intermediates and products are formed during a reaction. Mastery of this formalism is essential for accurately illustrating complex mechanisms.

Electrophilic Addition Reactions

Electrophilic addition reactions involve the addition of an electrophile to a nucleophile, typically across a double bond. In the context of the provided reaction, a bromine molecule acts as the electrophile, adding to the alkene to form a bromoalkane. Understanding the nature of electrophiles and nucleophiles is fundamental for predicting the products of such reactions and their mechanisms.

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