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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1:41 minutes

Problem 51h

Textbook Question

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

(h)

Verified step by step guidance

Step 1: Begin with methylenecyclohexane as the starting material. This compound contains a cyclohexane ring with a methylene group (CH2) attached via a double bond.

Step 2: Perform a hydroboration-oxidation reaction to convert the double bond into an alcohol group. Use BH3 (borane) followed by H2O2 (hydrogen peroxide) and NaOH (sodium hydroxide). This will yield cyclohexanol, where the OH group is added to the less substituted carbon of the double bond.

Step 3: To introduce the chlorine atom, perform a substitution reaction. React cyclohexanol with thionyl chloride (SOCl2) or phosphorus trichloride (PCl3) to replace the hydroxyl group with a chlorine atom, forming cyclohexyl chloride.

Step 4: To add the hydroxyl group back to the molecule, perform a nucleophilic substitution reaction. React cyclohexyl chloride with aqueous NaOH or KOH under controlled conditions to form the desired compound with both OH and Cl groups.

Step 5: Ensure the final product matches the target compound structure, with the hydroxyl group and chlorine atom attached to adjacent carbons on the cyclohexane ring.

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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 electrophiles to nucleophilic sites in alkenes. In the case of methylenecyclohexane, the double bond acts as a nucleophile, allowing for the addition of halogens or other electrophiles. This is a fundamental reaction in organic chemistry that can lead to the formation of various functional groups, such as halohydrins.

Halohydrin Formation

Halohydrins are compounds that contain both a halogen and a hydroxyl group on adjacent carbon atoms. The synthesis of halohydrins from alkenes typically occurs through the reaction of alkenes with halogens in the presence of water. Understanding this process is crucial for synthesizing the halohydrin compound shown in the question, as it illustrates how functional groups can be introduced to a carbon framework.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry deals with the spatial arrangement of atoms in molecules. In the synthesis of halohydrins from methylenecyclohexane, it is important to consider which carbon atoms the halogen and hydroxyl group will attach to, as well as the potential for different stereoisomers to form, impacting the final product's properties.

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(g)

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