课程名称︰有机化学 课程性质︰必带 课程教师︰杨吉水 开课学院：工学院 开课系所︰化工系 考试日期（年月日）︰2012/01/12 考试时限（分钟）：130 是否需发放奖励金：是 （如未明确表示，则不予发放） 试题 : 一.Multiple Choice Identify the choice that best completes the statement or answers the question. 1.Rank the following compounds in the order of increasing pKa of the bold proton: (i) (ii) (iii) (iv) OH O OH ／＼／ OH ║ ｜ ｜○｜ ｜ ／＼ H ＼／ ／ OH A)(i)<(iii)<(ii)<(iv) B)(iii)<(i)<(iv)<(ii) C)(iv)<(i)<(ii)<(iii) D)(ii)<(iv)<(i)<(iii) E)(iii)<(iv)<(i)<(ii) 2.Cyclohexanone reacts with D2O in the presence of NaOD to give tetradeuteriocyclohexanone. O O ／| ║ D ║ D _|_| ／＼ NaOD D_\／＼/_D ／_| ＼╴O ｜　｜ ───→ ｜　｜ ￣ ＼／￣ ＼／ D2O ＼／ AA Based on these conditions, how many protons in AA would undergo H/D exchange? A)0 B)1 C)2 D)3 3.Considering the compounds on both ends of the arrows only, which of the following reactions is NOT an oxidation process? A) H2O2 + - R3N ───→ R3N─O B) OH R' KMnO4 ｜ R' ／〝／ ───→ ／＼／ R R ｜ OH C) R' MCPBA O R' ／〝／ ───→ / \￥ R ◢ ￣ R D) OH 1)NaH OEt ／＼／ ───→ ／＼／ 2)EtI 4.Which of the following comparison between carbon radicals and carbocation is TRUE? A)Both are electron-deficient species. B)Both are charged species. C)Both are able to undergo rearrangement to produce the most stable species. D)Both would be destabilized by adjacent electron-withdrawing groups. E)Both are formed exothermically. 5.Provide the reagent(s) required to complete the following transformation: 　　　　　　　　　　　　　　　　　　　　　　　　　　　　　 　　　 ｜ 　　　　 　Br ＼／ 　　　　　　　　　　　　　 ＼╴／＼ ?? ￥￥ /￣\ ──→ ◤/￣\◥Br + En ＼／　　　　　　 　＼／　　　　　　　　　　　　　　 A)HBr B)Br2/hv C)Br2 D)HBr/ROOR E)hv/NBS 6.Predict the products of the following reaction: 1)O3 ╴== ────→ ＼〃 ￣ 2)DMS ｜ 3)H2O O O O O ║ ║ ║ ║ 　 ／＼ O═C═O ／＼ ／＼ ／＼ ／＼ H H OHC OH COOH OHC CHO I II　　 III IV V VI A)I,III,IV B)II,III,IV C)I,III,V D)II,IV,VI E)III,IV 7.How many of the following reaction would NOT give the indicated product? (i) (ii) ＿==＿／ Na ╴ ＼╴ HBr ＼／＼ ￣ ＼ ───→ ／￣＼＿／ ／￣ ───→ ｜ Br NH3 ＼ ROOR (iii) (iv) 1)Mg OH 2)CH2O OH 1)TsCl,py Cl ／＼／ ───→ ／＼／＼ ▼ ───→ ▼ Br 3)H3O+ HO OH ／＼ 2)NaCl ／＼ (v) 1)NaH ｜ ／＼／＼ ───→ ／\＼ ／＼／＼ OH 2) ｜ O ／\＼ Br A)1 B)2 C)3 D)4 E)5 8.Which sequence of reactions is expected to produce the product below as the final, and major, organic product? OH ▕＼╴==╴D ──→▕＼＿◤ + Enantiomer ▕／ ￣ ▕／ ＼＿D ￥ OH A)1)H2,Lindlar's cat.;2)MCPBA;3)H3O+ B)1)H2,Pt ;2)OsO4 ;3)NaHSO3/H2O C)1)H2,Lindlar's cat.;2)OsO4 ;3)NaHSO3/H2O D)1)Na,NH3(l) ;2)OsO4 ;3)NaHSO3/H2O E)1)Na,NH3(l) ;2)MCPBA;3)H3O+ 9.How many of the following reactions would proceed with retention of configuration of the chiral center? (i) OH (ii) OH (iii) O ▼ PBr3 ｜ ◥￥ conc.HCl ║ 1)LAH ＼／＼ ──→ ／＼／＼／ ───→ ／＼ ──→ 　　　　　　　　　　　　　　　　　　　　　　　　　O 2)H2O (iv) (v) Br ▼ ／＼ Br2 ▼ NaCCH ／＼／ 　▼ ──→ ／＼／＼ ───→ ／＼／ hv A)0 B)1 C)2 D)3 E)4 10.Consider the following route. How many of the following statements is TRUE? - + 1)9-BBN 　　／＼〃 HBr HC≡C Na ／────→ DD 　 ｜　｜ ───→ BB ────→ CC 2)NaOH 　　＼／ ROOR ＼ ＼H2SO4,H2O ＼──→ EE HgSO4 (i)BB is formed via cationic intermediate. (ii)CC is formed via SN2 pathway. (iii)DD and EE are diastereomers. (iv)The most acidic proton of CC can be deprotonated by NaOH. (v)DD and EE can be converted to each other via tautomerization. A)1 B)2 C)3 D)4 E)5 11.Which of the following sequence efficiently converts 2-methylpropene and sodium acetylide into 3-methylbutanal? O ｜ ?? ｜　║ 〃＼ ──→ ／＼／＼ H 3-methylbutanal A)1)HBr;2)NaCCH;3)O3;4)H2O B)1)HBr;2)NaCCH;3)O3;4)DMS C)1)HBr,ROOR;2)NaCCH;3)O3;4)H2O D)1)HBr,ROOR;2)NaCCH;3)H2/Lindlar's catalyst;4)O3;5)DMS E)1)NaCCH;2)H2/Lindar's catalyst;3)O3;4)DMS 12.How many of the following reactions give enantiomeric pairs as major products? (i) (ii) O (iii) ｜ H2 ║ 1)MeMgBr ／＼ NBS ／〝／＼ ──→ ／＼ ───→ ║　║──→ ｜ Pt Ph Et 2)H3O+ ＼／ hv (iv) - + (v) O Br HC≡C Na ║ NaBH4 ▼ ───→ ／＼／＼ ───→ ／＼／ ▲ MeOH A)1 B)2 C)3 D)4 E)5 13.Predict possible product(s) of the following reaction. ／ hv ｜ ──→ ／＼／◣ Cl2 ｜ ｜ ｜ ｜ ｜ ／＼／ ／＼／ ／＼／ ／＼／ ／＼／◣ ｜ ◢￥ ｜ ￥ ｜ ◣ ｜ ◢￥ ｜ ▲ Cl ＼ ＼ Cl 　　 Cl Cl I II　　　　　III IV V A)I B)I,II C)I,II,IV,V D)I,III,IV,V E)I,II,III,IV,V 14.Which of the following reaction products are optically active products? A) OH Na2Cr2O7 ／＼／ ────→ ▲ H2SO4,H2O B) O ║ 1)xs MeMgBr ／＼ ─────→ ▲ OEt 2)H2O C) O ║ NaBH4 ＼／＼ ───→ D) ／ Br2 ／＼◢＼ ──→ \ /￥ hv ￣ E) Br ｜ ▼ NaH ＼／＼ ──→ ▲ ｜ OH 15.Which of the ketones below could NOT be prepared by an acid-catalized hydration of an alkyne? O O O O O ║ \/ ║ ║ \／ ║ \／ ║ 　 ＿／＼／＼＿ ＼／＼ ＿／＼／￣ ＿／＼／￣ ＿／＼ ／\ /＼ ｜ ／\ ／\ ｜　 ／\ ｜ I II III IV V A)I B)II C)III D)IV E)V --

※ 发信站: 批踢踢实业坊(ptt.cc) ◆ From: 61.224.135.14