Problem Set 5: Organic Chemistry Reactions with Stereochemistry - Chem30B_Winter_2003 - Pr, Assignments of Organic Chemistry

Download Problem Set 5: Organic Chemistry Reactions with Stereochemistry - Chem30B_Winter_2003 - Pr and more Assignments Organic Chemistry in PDF only on Docsity! O Ph Ph OH O O Ph Ph O O H O Ag2O Br H O HO OH O OH O Br O O OH OH OH NH2 Ph Ph O PhPh Ph OPh O HD_30BWinter2003Page 1 of 4 Chem30B_Winter_2003 Prof. Miguel A. Garcia-Garibay TA: Hung Dang, dang@chem.ucla.edu 1) Draw the structure for the following compounds. Pay attention to stereochemistry. - Problem Set 5 - KEY isopropyl phenyl ketone 2,2-diphenyl cyclohex-3-enone cis-2,6-diphenyl cyclohexanone 1,1-dibenzoyl- cyclobutane 2) Provide the product(s) for the following sequence of reactions. Pay special attention to stereochemistry. a) 1) O3 2) DMS 3) LiAlH4 4) H3O + workup b) 1) NaCN 2) H3O + workup 3) H2, Pd c) 1) PBr3 2) PPh3 3) NaNH2 4) 5) H2, catalyst 3) Provide the product(s) for the following one-step reactions. Pay special attention to stereochemistry a) b) H+ cat. O O Ph O H O H MgBr O Ph Ph PPh3 O H A HA Ph O Ph H Ph O Ph H HO OH Ph O H O HO Ph H A Ph O H O Ph OH H A Ph O H O Ph OHH -H+ HH -H2O Ph Ph HO OH N NH2 Ph OH HO Ph H Ph O Ph OH Ph O Ph OH OO A Ph OH OH Ph H Ph Ph OOH Ph Ph OO HD_30BWinter2003Page 2 of 4 - Problem Set 5 - KEY c) d) e) 3) Provide the product(s) for the following one-step reactions. Pay special attention to stereochemistry Zn(Hg), HCl NH2NH2, Benzene Reflux 1) 2) H3O + workup + f) 4) Propose a DETAILED mechanism for the following reactions, using the proper curved arrows. Every step must be shown for full credit. (i.e. the initial (H+) protonation step from the acid catalysis.) H-A catalyst (-H2O) a)