Organic Chemistry Exam(A) Final Chinese Name: Student ID: Credit Question 1 2 3 5 Total Credits 1.Name the following compounds in English(IUPAC)or in Chinese(CCS)(20) IUPAC: IUPAC: 间○om ④入0入 IUPAC: IUPAC: ⑤√入入 】 IUPAC: IUPAC: o IUPAC: IUPAC: (0)Br CCS: 2.Answer the following questions(20) (1)Identify which of the following compounds possess optical activity h d h b Ph Newmann Project =0 H-OH Me
1 Organic Chemistry Exam (A) Final Chinese Name: Student ID: Credit: Question 1 2 3 4 5 Total Credits _____________________________________________________________________ 1. Name the following compounds in English (IUPAC) or in Chinese (CCS) (20) (1) (2) Cl Br IUPAC: IUPAC: (3) (4) (5) (6) (7) (8) (9) (10) OH O IUPAC: IUPAC: IUPAC: IUPAC: Cl H Cl H IUPAC: IUPAC: Br CCS: H Br Cl H CCS: 2. Answer the following questions (20) (1) Identify which of the following compounds possess optical activity. H CO2Et EtO2C H Br Bu-t a b c d CO2H HO H CO2H HO H OH Br MeO a: b: c: d: (2) Draw stable conformations for the following compounds Cl OH Me H Ph O a b Newmann Project
(3)Put the following intermediates in indicated orders. a QOO-w Stability increasing order: b Me3C,CHa.Me2CH,CHaCH2 Stability increasing order. (4)Identify the stereochemical relationships of the following structures (identical,enantiomer,diastereomer). a Ph C年9 a b: 3.Predict major products for following reactions,and indicate the stereochemistry if optional.(30) (1) 、人人 2龄5oH ②人入 H20,H 同人入a购，0 PhCH2CI Hao' w○ Os04,H202 o MCPBA EtOH,H' CH2Cl2.Na2CO3 TsCl,Py AcOK Hou. a
2 (3) Put the following intermediates in indicated orders. a b CH2 + + + Stability increasing order: Me3C. , CH3 . , Me2CH. , CH3CH2 . Stability increasing order: (4) Identify the stereochemical relationships of the following structures (identical, enantiomer, diastereomer). H Ph HO Ph H OH a b H Ph HO OH H Ph Cl H H Cl H Cl H Cl a: b: 3. Predict major products for following reactions, and indicate the stereochemistry if optional. (30) (1) (2) 1, B2H6, THF 2. H2O2, NaOH H2O, H+ (3) (4) (5) (6) (7) (8) Cl Mg, Et2O PhCH2Cl H3O+ OsO4, H2O2 MCPBA CH2Cl2, Na2CO3 EtOH, H+ OH TsCl, Py AcOK Br EtONa Br2, CCl4
HighT (12) =一品地0 w-○=sa,o4s0 入0ysm 4.Write stepwise and reasonable mechanisms for the following reactions(20) 0今cH,+ck500℃ ◇·
3 (9) (10) (11) (12) (13) (14) (15) O O O + High T 1. Na, NH3 (l) 2. EtOH OH PCC, CH2Cl2 HgSO4, H2O, H2SO4 O Br2, hv 4. Write stepwise and reasonable mechanisms for the following reactions (20). CH3 + Cl2 500 oC (1) Cl OH + HBr Br (+) (2)
5.Synthesize the following organic compounds with provided starting materials and necessary inorganic reagents.(10)[*Note:(3)is additional question with 5 point bonusl Starting materials:Toluene (MeC.NBS,1-corbutane than carbon atoms organic compounds
4 + HBr Br (3) Br + EtSNa (4) SEt 5. Synthesize the following organic compounds with provided starting materials and necessary inorganic reagents. (10) [*Note: (3) is additional question with 5 point bonus] Starting materials: Toluene (MeC6H5), NBS, 1-chlorobutane and no more than 4 carbon atoms organic compounds. O (1) (2) (3)* O