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

10. Addition Reactions

Markovnikov

Organic Chemistry

10. Addition Reactions

Markovnikov

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7: minutes

Problem 43b

Textbook Question

To which carbon would you expect an electrophile to add (1, 3, or 4)? Explain your answer.

Verified step by step guidance

Step 1: Analyze the structure provided in the image. The molecule contains two double bonds, one between carbons 5 and 6, and another between carbons 1 and 2. Carbon 3 and carbon 4 are single-bonded carbons connecting these two double bonds.

Step 2: Consider the concept of electrophilic addition. Electrophiles are attracted to regions of high electron density, such as double bonds. The addition of an electrophile typically occurs at the most electron-rich or reactive site.

Step 3: Evaluate the stability of the intermediate carbocation that would form after the electrophile adds. The stability of carbocations is influenced by resonance and hyperconjugation. In this molecule, adding an electrophile to carbon 3 would result in a carbocation that is stabilized by resonance with both double bonds.

Step 4: Compare the reactivity of carbons 1, 3, and 4. Carbon 1 is part of a terminal double bond, which is less stabilized by resonance. Carbon 4 is a single-bonded carbon and does not directly participate in resonance stabilization. Carbon 3, however, is in a conjugated system and can form a resonance-stabilized carbocation.

Step 5: Conclude that the electrophile is most likely to add to carbon 3 because it leads to the formation of the most stable intermediate carbocation due to resonance stabilization with both double bonds.

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Key Concepts

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

Electrophilic Addition

Electrophilic addition is a fundamental reaction in organic chemistry where an electrophile reacts with a nucleophile, typically across a double bond. In this process, the electrophile adds to the carbon atom of the double bond that can stabilize the resulting carbocation. Understanding this mechanism is crucial for predicting the product of reactions involving alkenes and alkynes.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen or other substituent) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This rule helps predict the major product of electrophilic addition reactions, guiding chemists in understanding regioselectivity in organic reactions.

Stability of Carbocations

The stability of carbocations is a key factor in determining the outcome of electrophilic addition reactions. Carbocations are positively charged species that can vary in stability based on their substitution; tertiary carbocations are more stable than secondary, which are more stable than primary. This stability influences which carbon atom an electrophile will add to, as the more stable carbocation intermediate is favored.

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