課程名稱︰有機化學 課程性質︰ 課程教師︰方俊民 開課學院：生農 開課系所︰農藝動科昆蟲 考試日期（年月日）︰100/6/21 考試時限（分鐘）：110 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 : I.Simple choice(36%) There is only one correct answer in each question. 1.Which compound has the highest acidity? (A) cyclohexanol (B) phenol (C) 2-nitrocyclohexanol (D) 4-nitrophenol 2.Which is a major product obtained from the reaction of ethylbenzene(C6H5CH2 CH3)with Br2/FeBr3? (A) C6H5CHBrCH3 (B) C6H5CH2CH2Br (C) 3-BrC6H4CH2CH3 (D) 4-BrC6H4CH2CH3 3.Which compound shows the highest reactivity toward HNO3/H2SO4? (A) nitrobezene C6H5NO2 (B) phenol C6H5OH (C) toluene C6H5CH3 (D) benzoic acid C6H5CO2H 4.Which reagent is used to convert toluene to benzoic acid? (A) K2Cr2O7 (B) NaOH (C) H2SO4 (D) NaCO3 5.Which atom or group on the bezene ring can direct the substitution of the incoming electrophile to the meta-position? (A) Cl (B) CH3 (C) CN (D) OH 6.Which compound has the highest basicity? (A) ethanamine CH3CH2NH2 (B) acetamide CH3CONH2 (C) acetonitrile CH3C≡N (D) aniline C6H5NH2 7.The pKa value of NH4+ is 9.26. What is the pKb NH3? (A) 0.74 (B) 4.74 (C) 9.26 (D) 14.0 8.The reaction of propanal CH3CH2CHO with NaOD/D2O can give the product (A) CH2DCH2CHO (B) CH3CHDCHO (C) CH3CH2CDO (D) CH3CH2CD2OH 9.Which compound is formed when benzaldehyde reacts with hydroxylamine H2NOH at room temperature? (A) 3-aminobenzaldehyde (B) 2-hydroxybenzaldehyde (C) benzaldehyde oxime C6H5CH=NOH (D) benzamide C6H5CONH2 10.Grignard reagent can be generated by the reaction of an alkyl halide RX with (A) Mg (B) Mg(OH)2 (C) MgBr2 (D) MgO 11.Which compound can react with Tollens' reagent (AgNO3/NH4OH solution) to form "silver mirror"? (A) 1-pentanol (B) 2-pentanone (C) pentanal (D) pentanoic acid 12.Which compound has the highest acidity? (A) 2-methylpropanoic acid (B) 2-chloropropanoic acid (C)3-chloropropanoic acid (D) 3-bromopropanoic acid 13.Which name is correct for the compound O=CHCH2CONHCH3? (A) 1-methyl-3- oxopropanamide (B) N-mthyl-3-oxopropanamide (C) 1-methyl-3-oxopropanamine (D) N-mthyl-3-oxopropanamine 14.An intramolecular amide is called (A) lactam (B)lactone (C)lactose (D) lactate 15.What can be generated when bemzoyl acetic acid C6H5COCH2CO2H is heated to 120。C? (A) CO2 (B) H2O (C) acetic acid (D) benzene 16.Which compound contains the most acidic α-H? (A) CH3CO2CH3 (B) CH3CH2CO2CH3 (C) CH2(CO2CH3)2 (D) PhCH(CO2CH3)2 17.Which compound can undergo self-aldol reaction? (A) formaldehyde (B) bezaldehyde (C) 2-propen-1-al (D) butanal 18.The tautomer of propanal CH3CH2CHO is (A) CH3COCH3 (B) CH2=CHCH2OH (C) CH3CH=CH(OH) (D) CH2=CH—OCH3 II.(5%) Classify the following species as aromatic or not aromatic. (A) — (B) H H (C) H (D) H (E) === // \\ ﹨∕ ∣⊕ ∣﹣ ／ ＼ ＼..／ ／＼ ／＼ ／＼ ∥ ∥ N ∥ ∥ \\__// \\__// ＼===／ | \../ H N H Ⅲ(6%) Show the reagents for conversion of acetophenone(1) to acetal 2,amine 3 and alkene 4. ＿_ O ∣ ∣ ∥ O O H NHCH3 ∥ ／＼／＼ ／＼╳ ／＼╳ ／＼／＼ ∣○∣ CH3 ∣○∣ CH3 ∣○∣ CH3 ∣○∣ CH3 ＼／ ＼／ ＼／ ＼／ 1 2 3 4 Ⅳ(8%)The reaction of 1-bromobutane with excess ammonia gives a mixture containing primary,secondary and tertiary amines as well as a quaternary ammonium salt.Show the structures of these products and their chemical names. Ⅴ(6%)What products will be obtained from the reactions of compound A? 1.Catalytic hydrogenation of compound A (H2,Pd/C) 2.Recation of compound A with NaBH4 in EtOH 3.Recation of compound A with LiAlH4 in Et2OH, and workup with water. Ⅵ(5%)Choose from the list of compounds A-G ＿＿ OH ／ ＼ //＼ ／＼／\\ ／＼／＼／ H2N— ○ —NH2 Cl ∣○∣ HO ＼＿＿／ ＼／ A B C D ／＼／＼／＼ O ∣ O ／＼ ∣ ＼ ∥ O ∣○∣ O＝C＝N ∣ N＝C＝O ／＼／\\O ／＼／＼ ／ ＼／＼／ ＼／＼／ ∣○∣ ∣○∣ O ∥ ∣○∣ ＼／＼//O ＼／ O ＼／ ∣ ／ O ∣ ＼／＼／＼／ E F G 1.The monomer for preparation of PVC 2.The two compounds for preparation of PU (polyurethane) 3.Plasticzer,an additive to increase the plasticity of polymer 4.Radical initiator for chain growth polymerization Ⅶ(14%)Some basic structures are given to help you answer questions. D-Glucose L-Alanine Adenine β-D-Ribofuranose Phosphoric (都會給結構式) 1.Which carbon in D-Glucose has the S-chirality? 2.Draw the chair conformation of β-D-Ribofuranose. 3.Draw the zwitterionic structure of D-Alanine (D-Ala),the enantiomer of L-Alanine 4.Draw the structure of dipeptide D-Ala-D-Ala 5.Given pKa values of COOH and NH3+ in L-Alanine are 2.35 and 9.87, respectively.What is the isoelectric point(pI) of L-Alanine? 6.Draw the structure of adenosine,a nucleoside derived from adenine and ribose 7.Draw the structure of adenosine 5'-triphosphate (ATP) Ⅷ(20%)Show the chemical structions and reagents to complete the following transformations. ∣ ∣ ∣ ／＼／＼ (A) ／＼／＼ (B) ／＼／＼ H2O ∣○∣ → ∣○∣ → ∣○∣ —→ (C) ／＼／＼ ／＼／＼ ／＼／＼+ heat NO2 NH2 N≡N Cl- O 1)2 equiv CH3MgBr ／ ╲=O ————————→ C6H14O2 (D) \___/ 2)H3O+ ＿＿ ／ ＼ NaOH ,EtOH O＝ ＝O ——————→ C6H8O (E) ＼ ／ heat HOH2C OCH3 (F) HOH2C NH2 (G) NH2 ＼／＼／ → ＼／＼／ → ／＼／＼／ ∥ ∥ HO O O O ∥ Br2,CH3COOH ／＼／ —————→ C8H13BrO ∣ ∣＼ ＼／ O OH O OH \\／ \\／ ∣ OH (I) ∣ O ／＼／ → ／＼／ ＼／ ∣○∣ ∣○∣ ∥ ＼／ ＼／ O O O O ∥ (J) ∥ ∥ ／＼ → ／＼／＼ H3C OCH3 H3C OC2H5 --

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