Question

146 ChemActivity 10: Oxidation and Reduction Model 8: Stereoselective Oxidative Cleavage of a x Bond Synthetic Transformation 10.9: Syn Addition of Two OH Groups to ax Bond H OH но OsO4 or OH NaHSO a cold, dilute KMnO, solution, followed by KOH can be used in place of the highly toxic OsO Review of Synthetic Transformations 9.3/9.4 H HOHO OH acide ring opening eр МCРВА or 1) Кон. 2) neutrize with dilute acid basic ring opening он Critical Thinking Question 20. Label one diol in Model 8 trans and the other cis. 21. Describe how each intermediate product in Model 8 dictates that the two OH groups will be added syn (same side-cis) or anti (opposite sides-trans) to one another. !!) Model 9: Oxidative Cleavage of the Entire C-C Bond (both a and Synthetic Transformation 10.10: Ozonolysis Think of these reactions as "cut and cauterize" procedures performed on a double bond instead of a blood vessel. R R Rs 1) ozone (Os) O blood vessel 2) Zn, acetic acid R2 H Ra HI cut Synthetic Transformation 10.11: Permanganate (MnO) Rs Rs R R3 1) KMnO, (hot) 2) Hy MO cauterize H OH nnnn Critical Thinking Questions 22. Draw a line (the cut) through each C-C double bond that is broken in Model 9, and state what atom caps (cauterizes) the loose ends resulting from each cut?

Answer 1

here both the -OH groups care above the plane ic. in some direction so, it h as alchol molt here in Carbon t the -OH is upwards to the plane but in carbon 2 oh is downwards the plane. so, it is trams alchol. Hb 4202 A6H OH In this case in second step the reaction alone at the Os conter & not in carben center. so, there is no Stereochemistry change at C-center. 30, Cisdiol form. OH here the basic & attacks to the epeseide from the back side of the eposside and opens the ring so, the incoming - OH and the formed - Ot are in tram.

30 Jeun, ott In acidic condition fint the o' of epostide protonater, and then the ho attack at the e atom from the back side of epoxide ring so, the fomed product is tram alchal.

9. R. I,R3 t. 03 RTH Pozn, Acetic Rotoh Photo-23 Geld B Rę Here are R 1.KMO (not, RYO + o=** 1 H 2.4300 in both the case the cut ends an loose ends cautrized by ö atom. To