Intensive Organic Chemistry for Freshmen Due:March.23.2001 Problem Set 6 1. Draw products of the following reactions. a) OHHKCN, H2SO4slight excess ofKCN b) OHHHSSHZnCl2AHgCl2CH3CN, H2OB c) OHHNLiTHF 2. Explain the following observations. a) O+ H2OOHHO b) + H2OF2HCPhOOF2HCPhOHO OH c) OOHHOHOOHOHHOHOOHOHOHOH d) + H2OOHOOH 3. Attempt to explain the following facts. These are not simple questions and you may not find the answers in any textbook. Think!H3CO OCH3H3CO OHOvsstableunstable+ CH3OHH3CO ClCl OHOvsstableunstable+ HCl 4. Draw the product of this transformation and explain. BrH2O, H2SO4(H2O addition)1(IR v=1710 cm-1strong band) 5. Draw the products of the following reactions. a) OHOTsOHA b) CH3OCH2Cl methoxy methyl chloride (MOM-Cl) is also used as an alcohol protecting group. Explain in detail the mechanisms of both reactions (protection & deprotection) HOCH3OCH2ClEt3N (Base)CH2Cl2BHCl (aq)THFC(protection)(deprotection) c) OO1. BH3.THF2. H2O2, NaOH3. H3O+D d) OHOHOHTsOH, heat(solvent)E (Think twice)6. Complete the following synthetic sequence. BrOHOTsOHAMg metalEt2OB1. CO22. H3O+CdeprotectionH+D 7. Synthesize hydroxy ketone 1 from 2. Racemic product is OK, but extra credit for optically pure product. OOHOOH12 8. Prepare R-enantiomer of 4 from a racemic mixture. BrOHBrOH4(R)-3 9. Propose an enantioselective synthesis of intermediate 5 from the given starting material.