《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: (R)-3-Methylheptane CCS: (R3甲基庚烷 2.9 IUPAC (S.S)-4-Bromo-2-hexanol CCS: (S,S)-4溴-2-己醇 3.HTF IUPAC: (3R.4S)-3-Chloro-4-Fluorohexane H-CI ccs: (3R4S3-氟-4氯己烷 4. IUPAC (R.R)-1.2-Dichlorocyclopentane CCS: (RR)-1,2-二氯环戊烷 2.Stereochemistry(30) 1.Identify which of the following compounds possess optical activity.(8) Br CXY Answer:c,d. 2.Identify the relationship of the following structures (identical,nantiomer,diastereomer) a Ph b Ph H Ph H H Hph (1)a and b:enantiomers (0) (3)aand d:identical (4)bandc:diasteromers (5)b and d:enantiomers
1 《Organic Chemistry》(A) Midsemester with solution Name:_____________ Student ID. _______________ Credit: _________________ 1. Name the following compounds in English (IUPAC) and Chinese (CCS) (20) (R)-3-Methylheptane (R)-3-甲基庚烷 (S,S)-4-Bromo-2-hexanol (S,S)-4-溴-2-己醇 (3R,4S)-3-Chloro-4-Fluorohexane (3R,4S)-3-氟-4-氯己烷 (R,R)-1,2-Dichlorocyclopentane (R,R)-1,2-二氯环戊烷 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: c, d. 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: enantiomers (2) a and c: diasteromers (10) (3) a and d: identical (4) b and c: diasteromers (5) b and d: enantiomers 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). a b Ph F-H 〉F十Newmann ProjectB Ph Ph H Pn 3.Write stepwise and reasonable mechanisms for the following reactions(20) 1.Predict major product and write mechanism. 人 Br2 hvBr +'Br ·Br+Br→Br2 人B一人 +人r 购+人一”+B 人·人X 2火Br+EOH0e Xa一人一k业，思 ee·& 2
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 H F Ph F H Ph c Br 3. Write stepwise and reasonable mechanisms for the following reactions (20) 1. Predict major product and write mechanism. Br2, hv Br2 hν Br + Br Br + Br Br2 + Br + HBr Br + Br + Br Br2 + + Br . Br + EtOH 2. OEt Br HOEt O H Et - H OEt Et O H H OEt HOEt
4.Predict the major product of the following reaction(20) 1a 2)H0 2.Br入入OH KOH ) 3. NMeaBr Mg.Eo EtBr EtMgBr 5. H2S04 OH △ /OE MeSO2CI.EtgN
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 MgCl OH (±) O (±) D NMe3Br EtMgBr Ph OH OEt OSO2Me CN
5.Synthesize the following compounds from provided starting materials and other reagents(10) 2. ◇文一一哭 1
4 5. Synthesize the following compounds from provided starting materials and other reagents (10) 2. 1. OH OH Br SEt 1. OH HBr Br Mg Et2O MgBr O H3O OH 2. Br AcOK OAc NaOH OH TsCl Et3N OTs EtSNa SEt