Question

2. For the following transformations, please provide detailed conditions to give the designated product in maximum yield with minimum by-products. More than one step may be needed. [8 pts ea] o OMe Phoн OH

Answer 1

OH 1) H20l H₂SO4 2) Brz/H2O H2O + H₂SO4 130 + He sa — 5 hout the count H-O-H + H SOL O O-H + -H20 de protection HH2O NAOH Hyeo halogenetien Brominium ron J e Deprotenation 04 GY Brominium on belowthe plane

Naome V Home a) Oso4, Hoo Ho NMO еоне ome SN Mechanism Transition state. 1.-BC Vome D ome Csopot Hacemento sto m i ome H2O NMO 620, Hydrolyst true relation seven more oson is a selective reagent for sin Hydroxylation reaction th than one Togres Osmate ester HO it can be tydrolyses girer drol's (syn).

of 1) Mcpsa, chaly 7 LIBY HOy the Mechanism mcposa CHCl3 4 VAHY SM opening of epoxide by hallty follow Sny mechanism always less substituted OH Side @ Scanned with CamScanner

_H104./ Home TOH ph HION H2O Ha! OH HOOG HO I-00 HOIT -H20 tra IO3 we je HI 04/10 is a selective reagent for cleavage of 1, 2 dials into Carbonyl compounds Scanned with CamScanner