課程名稱︰有機化學 課程性質︰必帶 課程教師︰楊吉水 開課學院：工學院 開課系所︰化工系 考試日期（年月日）︰2012/01/12 考試時限（分鐘）：130 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 : 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 --

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