4. Which of the following reactions involves overall definitive sxnaddition acro

Question

4. Which of the following reactions involves overall definitive sxnaddition across an alkene? RR"PhCO2Ag. l2 " KOH Ho R R' R" benzene OH 1) 1 eq. Phl(OAc)2" 0.2 eq. LiBr OH AcOH, 95°C, 18 h 2) 1.5 eq. K2CO3 OH b. Eor Z MeOH, r.t., 24 h ligand cy 5 mol-% CuOTf(0.5 Tol) 6 mol-% ligand 0.5 eq Ph O 2 eq. KOAc toluene, 70°C, ~ 30 h R: Ar, vinyl R': Ar, iPr, tBu 1.2 eq. KMnO 12 eq. BnEt NCI HO R' CO2R" R: alkyl, H, Bn acetone r.t., 3 h, 0°C, 35 min R: H, Me R: alkyl, Bn OH (added after 3 h) o 1. n-BuMgBr, Cul (cat.) Me 2. MeCHO (95%) 5. Which of the following alkenes will react with HCl to give an achiral product? H3C CH3 Ph CH3 CH3

Explanation / Answer

4 . a and c is syn addition across alkene. 1st one is Woodward reation involving syn iodination. 3rd one syn dihydroxylation in presence of KMnO4.

5. HCl addition to (d) will give achiral product. Because H+ added to opposite to CH3 group and Cl- added to CH3 attached carbon. That's why cyclopropane ring will be symmetrical from any side.

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