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

9. Alkenes and Alkynes

Hydrogenation of Alkynes

Organic Chemistry

9. Alkenes and Alkynes

Hydrogenation of Alkynes

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5:12 minutes

Problem 12c

Textbook Question

Show how you would convert
c. cis-cyclodecene to trans-cyclodecene.

Verified step by step guidance

Step 1: Understand the problem. The goal is to convert cis-cyclodecene (where the substituents on the double bond are on the same side) to trans-cyclodecene (where the substituents on the double bond are on opposite sides). This requires a stereochemical change in the configuration of the double bond.

Step 2: Recognize that cis-trans isomerization can be achieved through methods that involve breaking and reforming the π-bond of the alkene. Common approaches include photochemical isomerization or catalytic isomerization using a metal catalyst.

Step 3: Consider photochemical isomerization. Expose cis-cyclodecene to UV light. The energy from the UV light excites the π-electrons in the double bond, temporarily breaking the π-bond and allowing free rotation around the single bond. When the bond reforms, it can result in the trans configuration.

Step 4: Alternatively, consider catalytic isomerization. Use a metal catalyst, such as palladium or platinum, under mild conditions. The catalyst facilitates the breaking of the π-bond and allows the molecule to rearrange into the trans configuration.

Step 5: After the isomerization process, confirm the stereochemistry of the product using spectroscopic techniques such as NMR or IR spectroscopy to ensure the conversion to trans-cyclodecene has been successful.

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Key Concepts

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

Geometric Isomerism

Geometric isomerism occurs due to the restricted rotation around double bonds or ring structures, leading to different spatial arrangements of atoms. In the case of cyclodecenes, cis and trans refer to the relative positions of substituents on the double bond. Understanding this concept is crucial for recognizing how the configuration affects the properties and reactivity of the compounds.

Reactions of Alkenes

Alkenes, such as cyclodecenes, can undergo various reactions to alter their structure, including hydrogenation, halogenation, and isomerization. To convert cis-cyclodecene to trans-cyclodecene, one might employ a reaction that facilitates the rearrangement of the double bond, such as a catalytic hydrogenation followed by a dehydrogenation step. Familiarity with these reactions is essential for understanding how to manipulate alkene structures.

Catalytic Hydrogenation

Catalytic hydrogenation is a process where hydrogen gas is added across a double bond in the presence of a catalyst, typically palladium, platinum, or nickel. This reaction can convert alkenes into alkanes, and in the case of cis-cyclodecene, it can also facilitate the formation of trans-cyclodecene through a controlled reaction pathway. Recognizing the role of catalysts and reaction conditions is vital for achieving the desired isomer.

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