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) ② IUPAC:(3.5S)-3.5-dimethyloctane IUPAC: a○oH 2R.5txame-5 ④入0 IUPAC:cydohexano IUPAC:1-propoxypropane ⑤)入今 〈口 IUPAC:(E)-2-hexene IUPAC:(Z)-2.5-dimethyIhex-3-ene 0 IUPAC:2-hexyne IUPAC:cis-1.3-dichlorocyclopentane ⑨)、个8 CCS:反式1甲基4-溴环己烷 d CCS:(R,风-1氯-3溴环戊烷 2.Answer the following questions(20) 3 (1)Identify which of the following compounds possess optical activity. b c EtOzC H d ZH HO-H eo HCOZEt HO-H O,H a:no b:optical activity c:optical activity d:no
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: 反式-1-甲基-4-溴环己烷 H Br Cl H CCS: (3S,5S)-3,5-dimethyloctane (2R,5R)-2-bromo-5- chlorohexane cyclohexanol 1-propoxypropane (E)-2-hexene (Z)-2,5-dimethylhex-3-ene 2-hexyne cis-1,3-dichlorocyclopentane (R,R)-1-氯-3-溴环戊烷 2. Answer the following questions (20) 3. (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: no b: optical activity c: optical activity d: no
(2)Draw stable conformations for the following compounds b Ph Newmann Project =0 H-OH Me 大 人H Me ph (3)Put the following intermediates in indicated orders. 'QOx○c b MegC.CHg.Me2CH,CHgCHz Stability increasing order.CH3 CHaCH2,Me2CH,MeC. (4)Identify the stereochemical relationships of the following structures (identical,enantiomer,diastereomer). a Dh 6 4 a:Diastereomers b:identical 4.Predict major products for following reactions,and indicate the stereochemistry if optional.(30) 2
2 (2) Draw stable conformations for the following compounds Cl OH Me H Ph O a b Newmann Project Cl O Me H Ph O H (3) Put the following intermediates in indicated orders. a b CH2 + + + Stability increasing order: Me3C. , CH3 . , Me2CH. , CH3CH2 . Stability increasing order: CH2 + + + CH3 . , CH3CH2 . , Me2CH. , Me3C. , (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: Diastereomers b: identical 4. Predict major products for following reactions, and indicate the stereochemistry if optional. (30)
(1) 2芯6oH H20,H OH ( 3)入入Br Mg.E0 入√入MgBr PhCH2CI HgO* 〈Ph OH 0s04,H202 OH ,() OH MCPBA- EtOH,H' CH2Cl2.Na2CO3 () 6) () 、TsC,Py OTs AcOK OA 8)Br.CC4 +
3 (1) (2) 1, B2H6, THF 2. H2O2, NaOH H2O, H+ (3) (4) (5) (6) (7) (8) Br Mg, Et2O PhCH2Cl H3O+ OsO4, H2O2 MCPBA CH2Cl2, Na2CO3 EtOH, H+ OH TsCl, Py AcOK Br EtONa Br2, CCl4 OH OH MgBr Ph (+) OH OH (+) O (+) OH O (+) OTs OAc Br Br (+)
(12) 人=一/2：品N0 ) PCC.CHzCl2 人人0 00 (+) 5.Write stepwise and reasonable mechanisms for the following reactions (20). 0今cH+ch500℃ c1-C150c、2G 今H+c→入·+c 入·+ck→入+ 2CF CI-CI 2入·→入入 今·+c→今d
4 (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 O O O H H (+) O O O Br (+) 5. Write stepwise and reasonable mechanisms for the following reactions (20). CH3 + Cl2 500 oC (1) Cl Cl Cl 500o C 2 Cl. H + Cl. + HCl + Cl2 Cl + Cl. 2 Cl Cl Cl . + Cl. Cl 2
◇6·公 +) 。 cr.-c.c maio ④入+ESNa 人+EsNa SE 6.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 (MeCH).NBS,I-chorobutane and no more than4 carbon atoms organic compounds
5 OH + HBr Br (+) (2) OH + HBr Br (+) OH2 + -H2O + + Br- -Br- + HBr + Br major Br minor (3) Br H+ + BrBr + EtSNa (4) SEt Br + EtSNa Br SEt S SN2 6. 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
”① 6
6 O O (1) (2) (3)* NBS, CCl4 Br OH ONa NaOH NaNH2 BuBr H2, Lindlar catalyst NaNH2 BuBr HgSO4, H2O, H2SO4