Problem Set 1Intensive Organic Chemistry for Freshmen Due: 2.2.2001 Problem Set 1 1. Draw products of the following reactions. CCHNa NH2NH3(l), -33oCAO1.ethylene oxide2. H3O+B 2. BrOH1 eq BuLiEt2OC1 eq BuLiEt2ODO2. NH4Cl(aq)E 3. NCIEt2CuLiTHF, 0oCF 4. CH2I2, Zn-CuG 5. CHBr3OH-BrBr(CH3)2cuLiEt2OH How would you distinguish between products G and H? 6. Propose a reasonable mechanism for the following reactions. a) Br H2CuCNLi2THF, 0oCH b) 2CuCNLi2THF, 0oCBr7. Predict the product of this reaction and briefly explain. Pay attention to regio- and stereo-chemical issues. 2CuCNLi2THF, 0oC 8. Synthesize molecules 1 and 2 in the most efficient way (both are hot leads in a pharmaceutical firm X) from acetylene (C2H2). OHOHHCCH 9.a) HH+ 1 eq nBuLiA +OMeOB b) OOMe+LiC c) MgBr+ID 10. Transform bromobenzene to compounds 1 and 2.