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

Halohydrin

Organic Chemistry

10. Addition Reactions

Halohydrin

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2:09 minutes

Problem 46q

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.
(q)

Verified step by step guidance

Step 1: Analyze the reaction conditions. The reagents are Cl₂ and H₂O, which indicate a halohydrin formation reaction. This reaction typically involves the addition of a halogen (Cl₂) and water (H₂O) across a double bond in an alkene.

Step 2: Identify the starting material. The structure provided is a bicyclic compound containing a double bond. The double bond is the reactive site where the halohydrin formation will occur.

Step 3: Understand the mechanism. The reaction proceeds via electrophilic addition. First, Cl₂ interacts with the double bond to form a cyclic chloronium ion intermediate. This intermediate is highly strained and reactive.

Step 4: Nucleophilic attack by water. Water acts as a nucleophile and attacks the more substituted carbon of the chloronium ion, leading to the opening of the ring. This step results in the formation of a halohydrin, where a hydroxyl group (-OH) and a chlorine atom (-Cl) are added across the double bond.

Step 5: Consider stereochemistry. The addition of Cl₂ and H₂O is anti-addition, meaning the hydroxyl group and chlorine atom will be added to opposite faces of the double bond. This stereochemical outcome should be reflected in the major product structure.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions involve the addition of an electrophile to a nucleophile, typically across a double bond. In this case, the cyclohexene derivative acts as a nucleophile, reacting with chlorine (Cl2) as the electrophile. This reaction leads to the formation of a cyclic halonium ion intermediate, which is crucial for understanding the subsequent steps in the reaction mechanism.

Halohydrin Formation

Halohydrin formation occurs when a halogen and water add across a double bond, resulting in the formation of a halohydrin. In this reaction, after the formation of the cyclic halonium ion, water acts as a nucleophile, attacking the more substituted carbon, leading to the formation of a halohydrin product. This process is important for predicting the major products and their stereochemistry.

Stereochemistry in Organic Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of this reaction, the stereochemistry of the halohydrin product is influenced by the mechanism of the reaction, particularly the formation of the cyclic halonium ion. Understanding stereochemistry is essential for accurately predicting the configuration of the final products, including any chiral centers that may be formed.

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Related Practice

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(h)

Textbook Question

The solutions to Solved Problem 8-5 showed only how one enantiomer of the product is formed. For each product, show how an equally probable reaction forms the other enantiomer.

Textbook Question

Predict the major product(s) for each reaction. Include stereochemistry where appropriate.

e. 1-methylcyclopentene + Br₂ in saturated aqueous NaCl

Textbook Question

The solutions to Solved Problem 8-6 showed only how one enantiomer of the product is formed. For each product, show how an equally probable reaction forms the other enantiomer.

Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

5. Br₂ + H₂O

b. With which reagents do the two alkenes react to form different products?

Textbook Question

Show how you would accomplish the following synthetic conversions.

b. chlorocyclohexane → trans-2-chlorocyclohexanol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.

Textbook Question

What reagents are needed to carry out the following syntheses?

Textbook Question

Draw the products of the following reactions, including their configurations:

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