Dr. P. Wipf CHEM 2320 2/15/06 NAME: SID: Sample ExamSample Exam I (18 pts) ___________ II (18 pts) ___________ III (18 pts) ___________ IV (15 pts) ___________ V (15 pts) ___________ VI (16 pts) ___________ VII (Bonus) ___________ TOTAL (100 pts) ___________ This Exam has 8 pages.Page 2 Problem I. (18 pts) Predict the major products for the following reactions. Draw all products in the 3D conformations and make it clear what the product configuration is. a) ClONaBH4 b) O1. H2SO4, MeCN2. H2O c) HOBnOMgBr2•OEt2MgBrMeO2C d) Et CHOOMe+ButOLi e) OTBDMSOOMeOHHON+Me2Cl-ClCl f) OOOCHPh2OH(-)-DIPT, t-BuO2H,Ti(O-i-Pr)4, CH2Cl2Page 3 Problem II. (18 pts) Provide products for the following reactions. If relevant, indicate absolute and/or relative stereochemistry of the major expected product. a) Ot-BuO2H,BnMe3NOHTHF, H2O b) OPhEtMgI c) MCPBAH d) S SOPhLAH e) O OOPhMe MgBr f) BnOMCPBA, CH2Cl2, 0 °COHPage 4 Problem III. (18 pts) Propose methods for the following conversions. Use reagents as required. a) b) HHOSiMe3HSiMe3O c) NOAcOAcCO2BnNOAcCO2BnCOPh d) OOOH(Bonus points: what is the name of this reaction?) e) NHONMeOH f) OHPh2CHOOHPh2CHOOPage 5 Problem IV. (15 pts) Draw a (real!) reaction for which the Curtin-Hammett principle applies, and map out the reaction coordinate-energy diagram of this process.Page 6 Problem V. (15 pts) Provide three methods for the enantioselective synthesis of epoxides from achiral starting materials, including all the necessary reagents.Page 7 Problem VI. (16 pts) Based on the Cieplak and the Felkin-Ahn-Eisenstein (polar Felkin) models, what would be the major product(s) of the following addition reaction? Support your selection with orbital drawings of the transition state in the appropriate chair conformation, and explain, in a few words, the salient features of each hypothesis. PhOFMeLiPage 8 Problem VII. (Bonus) Draw the mechanisms of a typical Ritter
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