Question

Provide conditions for the following reactions. More than one step may be needed. Incorporate conditions that would give you the optimum yield, and be mindful of 1. stereochemical details. (4 pts each) a b. но ОН For each reaction below, please draw the starting material or the major (singular) product, including any pertinent stereochemical details. (3 pts each) 2. a. 3. Hg(OAc)2, D20 2. KOt-Bu 1.TsCl Он 4. NaBH t-BuOH EtgN etherol b. 3. СHBES 2. LDA 1. HBr KOt-Bu, t-BuOH THF ROOR C. 1.O3 2. Me2S

Answer 1

H N OLDA 2. a) Mechamsm H LOA OH Og04 H20

Mechanism ме OH GH2 И H OH OH Thnee gra inter cheryge in Thnee mcons thp ee fraajustenhe rpson

2.a) OTse /s OH OTS Et3 Ne Kot- Bu E- BuDH -OAe OD rone Na BHy 2.b RoH OR + Br ROOR+ HBr Br Br 30nadicalo more sladle dhen Becose 2 padical becolts ypepaonjeagolcon

Br LDA THF 7 CHBh3 KOt-Bu Cerz Br Br N. 1 03 2.e) 2. Mezs 02oner aton Mechanesm Mezs