Write arrow pushing mechanism for cyclohexene/oxone reaction. Indicate the proper stereochemistry.
2. Using Scifinder (see the note below) find a different oxidizing reagent that will result in cis stereochemistry. (Reference!) Hydrogen peroxide
Tadayonpour, Nasim, Saeed Rayati, Moayad Hossaini Sadr, Karim Zare, and Andrzej Wojtczak. "A Cis-dioxomolybdenum Schiff Base Complex: Synthesis, Crystal Structure and Catalytic Activity in Oxidation of Olefins Using Hydrogen Peroxide." Transition Metal Chemistry 40.8 (2015): 891-97. Web.
3. List two other TLC stains that would help visualize 1,2-cyclohexadiol. Vanillin and Iodine
4. Draw your TLC plate and explain in detail the results. The cis standard was placed into lane…show more content… Why is cis-1,2-cyclohexadiol less polar than trans. Explain in detail using figures. Cis is less polar because it is a meso compound and is therefore more symmetrical. Thus, the charges are more evenly distributed. The trans form is more stable due to less steric hindrance because the OH groups are both in equatorial positions.
6. What happens to oxone when quenched with saturated sodium bisulfate. Deactivates oxone and keeps it from oxidizing other compounds.
7. For the reaction using oxone you were asked to add acetone. What is it for? Oxone and acetone come together to form dimethyldioxirane.
8. 100% ethyl acetate was used as the eluent for TLC plate. a) What would happen if you used 50% ethyl acetate/hexane mixture? Compared to Ethyl acetate, hexane is less polar. Given the fact that TLC analyzes molecules based on their polarity. Using a less polar solvent would cause the polar molecules used in this experiment to not move as quickly because they wouldn't be as attracted to the solvent. This would cause a lower Rf and would make distinguishing the trans and cis isomers from one another more difficult. b) What would happen if you used 90% ethyl acetate and 10% methanol
