課程名稱︰有機化學 課程性質︰必修 課程教師︰楊吉水 開課學院：醫學院/生農院 開課系所︰醫技系/園藝系 考試日期（年月日）︰2011/03/31 考試時限（分鐘）：100分鐘 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 : (單選題，每題2分，共60分) 1. How many nonbonding electron pairs are in the structure shown below? CH3COOH a.2 b.4 c.6 d.8 e.none of above 2. Which of the following best represent the shape of a sp3 hybrid orbital of carbon. 選像是圖 (1. s orbital 2. p orbital 3. sp orbital 4. sp3 orbital) 3. Consider the formation of an sp2 hybrid orbital. Which of the following is true? a. Four equivalent hybrid orbital are produced. b. One s and one p orbital are involved. c. One p atomic orbital remain unhybridized. d. The hybrid orbitals produced can form pi bonds. e. None of the above. 4. How many electrons are there in the calence shell of the carbon atom of a methyl anion, CH3-? a.5 b.6 c.7 d.8 5. Which of the following statements is NOT true? a. The carbon-carbon single bond of an alkane is weaker than the carbon- carbon triple bond of an alkyne. b. The carbon-carbon triple bond of an alkyne is shorter than the carbon- carbon double bond of an alkene. c. The carbon-carbon triple bond of an alkyne is exactly 3 times as strong as a carbon-carbon single bond of an alkane. d. The carbon-carbon single bond of an alkane is longer than the carbon- carbon triple bond of an alkyne. 6. Name these groups (left to right). (結構圖) ANS: isopropyl, sec-butyl, isobutyl 7. In an organic reaction, which of the following is most likely to function as only a nucleophile? a.BF3 b.(CH3)2CHNH2 c.Fe2+ d.CH3CH2S- e.both a and c 8. Choose subdtituent X and Y (listed in order below) for the following cpd so as to make a Z isomer. Cl Y a. Br, NHCH3 \ / b. F, CHO C = C c. I, OCH3 / \ d. COOH, CH2NH2 X CN e. Br, COOH 9. An accurate description of the structure of benzene is: a. The pi bonds are quickly moving aronf the ring. b. There are teo distinct structure that are in equilibrium. c. All the carbon-carbon bonds are equil in length. d. There are distinct single and double bonds. e. Some bonds are longer than others. 10. What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide? a. nucleophilic addition b. electrophilic addition c. radical addition d. elimination 11. What is the IUPAC name of the following compound? (結構圖) ANS: 3-bromo-4-nitrobenzoic acid 12. The following reaction is commonly used as a laboratory preparation of cyclohexene. (結構圖: hydroxycyclohaxane -(H+,△)-> cyclohexene + H2O) The forward and reverse reaction are classified, respectively, as: a. addition, elimination b. elimination, substitution c. elimination, addition d. elimination, rearrangment e. substitution, addition 13. What is the major organic compound abtained from the following reaction? (p-methyl benzoic acid -(Br2, FeBr3)->) a. m-bromo-p-methyl benzoic acid b. o-bromo-p-methyl benzoic acid c. methyl group --> CH2Br d. COOH --> COBr 14. What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3? a. CH3C≡O+ b. CH3+ c. CH3COO- d. benzene 15. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reaction? a. Cl, CN, NO2 b. Cl, NH2, CH3 c. CH3, OCH3, COCH3 d. CH3, NH2, OCH3 16. How many pi electrons are present in imidazole? a.2 b.4 c.6 d.8 e.10 17. Place the following in order of reactivity towards electrophilic aromatic substitution. I. phenol II. chlorobenzene III. nitrobenzene IV. benzene－COCH3 18. What is the correct assignment of the names of the following aromatic compounds? (結構圖) ANS:aniline, pyrrole, pyridine 19. Which of the following heterocycles os aromatic? ＿ ＿　　　　　＿　　　　　_N 黃色=double bond ／　＼　　 / \ / \ / \ 　 ＼ˍN/ ＼／ ＼／ ＼／ S　 O NH 20. What type of reactive intermediate is involved in both 1.) reaction of alkene with Br2 in the present of H2O to give bromohydrin 2.) 2-step hydroxylation of an alkene a.carbocation b.carbanion c.radical d.cyclic bromonium ion e.cyclic ion 21. Consider the following 2 structure: CH3CH2OH CH3OCH3 Which of the following correctly describes the structure of these cpds? a. All carbon atoms are sp3 hybridized. b. All of the bonds are sigma bonds. c. Each oxygen atom has two nonbonding pairs of electron. d. The bond angle around each oxygen atom is similar and near 109.5。 e. All of the above 22. What is the formal charge on the nitrogen atom indicated in the following compound? CH3－CH2－N－N≡H: a.0 b.-1 c.+1 d.-2 e.+2 23. Rank the following in order of decreasing importance as a contributing resonance structure to the molecular structure of acetone, CH3COCH3. :O: +:O: ::O:- ∥ |- |+ C :C C / \ / \ / \ H3C CH3 H3C CH3 H3C CH3 24. Which of the following fuctional group classification do NOT contain O? a.ether b.thiol c.aldehyde d.ester e.amide 25. 4-methyl-3,3,4-trimethylheptane contains: a. 2 quaternary C atoms b. 2 tertiary C atoms c. 4 secondary C atoms d. a & c e. all of the above 26. If ethane reacts with a large excess of chlorine over a long period of time, the most likely major product of the reaction would be: a. CCl3CCl3 b. CH3CH3 c. CH2ClCH2Cl d. CH2ClCH3 e. Ethane does not react with the halogens 27. Which of the following Newman projections don't represent 2-methylhexane? CH3 CH(CH3)2 CH2CH3 H H H H H H3C H H CH2CH2CH2CH3 ○ ○ ○ ○ H CH3 H H H H H H CH2CH2CH3 CH2CH3 CH2CH3 CH3 28. Which of the following structure cycloalkanes has the most ring strain? a. cyclopropane b. cyclobutane c. cyclopentane d. cyclehexane 29. Which of the following structures represent trans-1,3-dimethylcyclohexane? (選項結構圖--hexane chair structure) 30. Which of the following correctly compares the 2 elements in terms of polarizability? a.S > O b.F > Br c.N > P d.Cl > I (問答題，共62分) 1. Is the bicarbonate anion a strong enough base to react with methanol? In other words, does the following reaction take place as written? Explain. (pka methanol=15.5; pka H2CO3=6.4) CH3OH + HCO3- ----> CH3O- + H2CO3 2. Draw an orbital picture al allene, H2C＝C＝CH2. What hybridization must be central carbon atom have to form 2 double bonds? What shape does allene have? 3. Give IUPAC names for the following compounds: (結構圖,課本習題內容) 4. One of the two chair structure of cis-1-chloro-3-methylcyclohexene is more stable than the other by 15.5kJ/mol. Which is it? 5. Consider the energy diagram shown: (習題能量圖) (a) Indicate the overall energy change for the reaction. Is it positive or negative? (b) How many steps are involved in the reaction? (c) Which step is faster? (d) How many transition states are there? Label them. 6. Draw 3 additional resonance structure for the benzyl cation. 7. Predict the product of the following reaction on dec-5-yne. dec-5-yne --(H2O, H2SO4, HgSO4)--> ? 8. Starting with benzene, how would you synthesize the m-bromobenzenesulfonic acid? Assume that you can separate ortho and para isomers if nessesary. 9. Draw the structure of a hydrocarbon that reacts with 2 equivalents of H2 on catalytic hydrogenation and gives only succinic acid on reaction with acidic KMnO4. Succinic acid => HOOC-CH2CH2-COOH 10. Draw the reaction mechanism of CH4 + Cl2 --> CH3Cl + HCl. (you should use curved arrows.) 11. Predict the structure of cyclooctatetraene. Explain your answer. 12. Draw the product and reaction mechanism (with curved arrows) on the following reaction: cyclohexene + Cl2 -----> (End. Good Luck!) --

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