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臺北醫學大學 101 學年度碩士班暨碩士在職專班招生入學考試
有機化學試題 本試題第 1 頁；共 3 頁 (如有缺頁或毀損，應立即請監試人員補發) ⊕ ⊕ 注 意 事 項 一、本試題共二大題，共計 100 分。 二、請將最適當的答案依題號作答於答案用卷本上。 三、試題答錯者不倒扣；題次號碼錯誤或不按順序或鉛筆作答，不予計分。 一、選擇題：(75%)1. Which of the following compounds have the molecular formula C6H14O?
1-hexanol 2-hexanal 3-methyl-2-pentene cyclohexanol 2. Which of the following is the most soluble in H2O?
CH3CH2OCH2CH3 CH3CH2OH CH3CH2CH2CH3 CH3CHO
3. (-)-Mandelic acid has a specific rotation of -158O
. What would be the specific rotation of a solution which contains 40% (-)-Mandelic acid and (+)-Mandelic acid?
+95 O
+63 O
-32 O
+32 O
4. Which of the following is a secondary alkylhalide?
CH3Br (CH3)3CBr (CH3)2CHBr (CH3)2CHCH2Br
5. Which of the following carbocations does not rearrange?
CH3CH2 CH3CHCH3 all the above
6. Which of the following molecular changes is necessary for mass spectrometry to occur? excitation of an electron from the ground state to higher energy state
loss of an electron
change of alignment of a proton in a magnetic field molecular vibration
7. Which of the following is the electrophile that attacks the aromatic ring during nitration?
NO2 HNO3 NO3－ NO2＋
8. Which of the following esters undergoes hydrolysis in base most easily?
C6H5O2CCH3 p-CH3C6H4O2CCH3 p-NO2C6H4O2CCH3 CH3CH2CO2CH3
9. Which of the following reagents is used in the following reaction?
Cl2/P Cl2/CCl4 HCl PCl3
10. Which of the following reagents can be used to reduce acetaldehyde to ethyl alcohol?
1. LiAlH4 2. H3O＋ 1. NaBH4 2. H3O＋ H2/Pt all the above
11. Which of the following compounds will give a positive iodoform test?
propanal 2-pentanone 3-pentanone cyclohexanone 12. Which of the following represents the general formula of a carbohydrate?
CnH2n+2 CnH2n CnH2n-2 Cn(H2O)n
13. Which of the following is the best leaving group? F－
Cl－
Br－
I－
14. Which of the following solvents is protic?
新聞稿
臺北醫學大學 101 學年度碩士班暨碩士在職專班招生入學考試
有機化學試題 本試題第 2 頁；共 3 頁
(如有缺頁或毀損，應立即請監試人員補發)
15. Arrange the following species in order of increasing basicity (weakest to strongest). OH－
Cl－
H2O NH3
16. Which of the following sets are pairs of constitutional isomers?
O O
‖ ‖
CH3CH2OCH3 and CH3CH2CH CH3CH2OCH3 and CH3CCH3
O O O
‖ ‖ ‖
CH3CH2CH and CH3CCH3 CH3CH2OH and CH3CH
17. Which is the structure for trans-1-ethyl-3-isopropylcyclohexane?
H
H H
H H
H
H H
18. Which is the IUPAC name for the following cycloalkane?
CH3 CH2CH3
cis-1-ethyl-2-methylcyclohexane trans-1-methyl-2-ethylcyclohexane cis-1-methyl-2-ethylcyclohexane trans-1-ethyl-2-methylcyclohexane 19. How many Z-isomers are there for an alkene with the formula C4H7Cl?
1 2 3 4
20. What is the R, S configuration for the following structure of isocitric acid?
OH O HO O OH O HO 2R, 3R 2R, 3S 2S, 3R 2S, 3S 21. What is the major contributing structure to the cation intermediate of the bromination of anisole?
H Br O H Br O H Br O H Br O I II III IV IV III II I
22. Which sugars and classifications are correctly matched?
I) D-Glucose and aldohexose II) D-Galactose and aldopentose III) D-Ribose and ketopentose IV) D-Fructose and ketohexose V) D-Mannose and ketohexose
I, III, V I, IV III, IV, V II, III 23. What is the relationship between the following compounds?
CH2OH H HO OH H H OH CHO CH2OH OH H OH H H OH CHO
新聞稿
臺北醫學大學 101 學年度碩士班暨碩士在職專班招生入學考試
有機化學試題 本試題第 3 頁；共 3 頁
(如有缺頁或毀損，應立即請監試人員補發)
24. Which of the labeled atoms is the anomeric carbon?
OH OCH3 OH OH CH2OH O a) b) c) d) a b c d
25. Which molecules are zwitterions?
H2NCCH2CH2CHCO O O NH3 HSCH2CHCOH O NH3 H2NCNHCH2CH2CH2CHCO O NH3 NH2 N H H CO O I II III IV
I, III II, III III, IV I, IV 二、問答題：(25%)
1. What are the structure of A, B, and C?(10%)
NBS hv A NaOCH2CH3 CH3CH2OH,heat B (C5H6) CH2=CHCO2H C 1. O3 2. S(CH3)2 CHO HOOC CHO
2. Calculate the index of hydrogen deficiency for the compound of formula C11H15NO.(5%)
3. Following are infrared spectra of compounds E and F: One spectrum is of 1-hexanol, the other of nonane. Assign each compound its correct spectrum.(5%)
4. Propose a chemical structure for C7H6Br2 according to its 1H NMR data. This compound contains an aromatic ring. 1
