Explore oxidation states and mechanisms in organic chemistry through this 47-minute lecture from Yale University's Freshman Organic Chemistry II course. Examine a challenging exam question on spectroscopy and triphenylmethyl dimer structure. Discover evidence supporting an SN2 mechanism in Friedel-Crafts propylation. Learn to assign carbon oxidation states from -4 to +4 and select appropriate oxidizing or reducing reagents. Investigate the mechanisms of alcohol oxidation by elemental bromine and Cr+6 reagents, understanding how to adjust conditions for selective oxidation. Gain insights into spectroscopy, reaction mechanisms, and oxidation processes to enhance your understanding of organic chemistry principles.