《Organic Chemistry》(A) Midsemester with Solution Name Student ID Credit 1.Name the following compounds in English(IUPAC)and Chinese(CCS)(20) 、人人 IUPAC: 2.9Hr IUPAC CCS: 3. H-F IUPAC H-CI ccs: IUPAC: ccs: 2.Stereochemistry (30) 1.Identify which of the following compounds possess optical activity.(8) Answer 2.Identify the relationship of the following structures(identical,enantiomer,diastereomer) c Ph 中 Ph P (1)a and b: (2)aand c: (10) (3)aand d: (4)b and c: (5)b and d: 1
1 《Organic Chemistry》(A) Midsemester with Solution Name:_____________ Student ID. _______________ Credit: _________________ 1. Name the following compounds in English (IUPAC) and Chinese (CCS) (20) 2. Stereochemistry (30) 1． Identify which of the following compounds possess optical activity. (8) H H H CO2H HO2C H Br Bu-t a b c d Answer: 2. Identify the relationship of the following structures (identical, enantiomer, diastereomer). H Ph F Ph H F a b c H Ph F H Ph F Ph F Ph F H H H Ph F F Ph H d (1) a and b: (2) a and c: (10) (3) a and d: (4) b and c: (5) b and d: Cl Et H Et H F 1. 2. OH Br Cl Cl 3. 4. IUPAC: CCS: IUPAC: CCS: IUPAC: CCS: IUPAC: CCS:
3.Draw stable conformations for the following compounds(12). H NesmnainPiged a b Ph Ph b 3.Write stepwise and reasonable mechanisms for the following reactions(20) 1.Predict major product and write mechanism. 人 2火B+EOH→oE
2 3. Draw stable conformations for the following compounds (12). H H Br H Ph F Ph F H a b c Newmann Project a b c 3. Write stepwise and reasonable mechanisms for the following reactions (20) 1. Predict major product and write mechanism. Br2, hv . Br + EtOH 2. OEt
4.Predict the major product of the following reaction(20) 1个a购9 2)H30* 2Br入OH KOH 3. 「E8r90 PhCH2CI △ 6. EIOH.H" 。 KOH EtOH MesO2CI,EtgN NaCN
3 4. Predict the major product of the following reaction (20) Cl 1. EtBr Mg, Et2O 1) 2) H3O+ H O 2. 3. D Br Me3N 4. Br OH KOH 5. H2SO4 6. OH MeSO2Cl, Et3N NaCN 7. O EtOH, H+ 8. Br KOH Mg, Et2O PhCH2Cl OH EtOH
5.Synthesize the following compounds from provided starting materials and other reagents(10) 、一一·哭
4 5. Synthesize the following compounds from provided starting materials and other reagents (10) 2. 1. OH OH Br SEt