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注 意 事 項 一、本試題共 30 題，共計 100 分。 二、請將最適當的答案依題號作答於答案卷上。 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。I. Give the IUPAC names of the following two compounds, if possible with proper R/S or E/Z designations. (8%, 4% each) 1.
2.
II. Give the products of the following reactions. (8%, 4% each) 3.
4. What are the compound of A1 and A2? Give their structures.
NH2
Na
III. The following items will be used to answer the questions 5-7. (9%, 3% each) AlCl3 ? NaNO2, HC1 0℃ CuO Cu(NO3)2,H2O A1 A2 H (#32) (#32) H (#33) H (#34) (#35) (#36) (#37) (#38) (#39) (#40) (#41) (#42)
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5. For the compounds (#32)~(#35), what is the order of their acidity?
(#35) < (#34) < (#33) < (#32) (#32) < (#34) < (#33) < (#35)
(#32) < (#33) < (#34) < (#35) (#32) < (#35) < (#33) < (#34)
6. The product of the following reaction is ?
(#36) (#37) (#38) (#39)
7. The dehydration product of the following reactions is ?
(#39) (#40) (#41) (#42)
IV. The following items will be used to answer the questions 8-9. (6%, 3% each)
OC2H5 O OH OC2H5 O O OH O OH O (#43) (#44) (#45) (#46) O O O OC2H5 O O OH (#47) (#48) (#49) (#50)
8. The product of the following reaction is ?
OC2H5 O
1)NaOC2H5 2) HCl, H2O
(#43) (#44) (#45) (#46)
9. The product of the following reaction is?
OEt
O
OEt O
1. NaOEt, 2. H2O/HCl
3. saponificaiton, 4. acidification heat
(#47) (#48) (#49) (#50) H O NaOH aq H2O + ? NaOH(aq) OC2H5 OC2H5
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V. The following items will be used to answer the question 10.
O COOH HOOC O HOOC O COOEt EtOOC O HOOC (#51) (#52) (#53) (#54)
10.The product of the following reaction is ? (3%)
OEt OEt O O + O 1) NaOEt/EtOH 2) Saponification 3) acidification 4) heat (#51) (#52) (#53) (#54)
VI. Show the reagents and conditions to complete the following synthesis. (11-12) . (8%, 4% each) 11. 12. ? COOH Cl
13.Please draw curved arrows to complete the following conversions: (4%)
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VII. Multiple choice. (42%, 3% each)
14.Which of the following compounds is a tertiary (3°) alcohol?
I II III IV
I II III IV
15.Arrange the following species in the order of increasing acidity (weakest to strongest). I. H2O II. H3O+ III. NH4+
II, III, I I, II, III III, II, I I, III, II
16.Which of the following belong in the group of constitutional isomers for C3H6O2?
II, III II, IV, V I, II, V I, V
17.Arrange these carbocations in order of increasing stability (least to most).
I, II, III I, III, II II, I, III III, II, I
18.Which of the following structures have correct common names?
I, III III, IV I, II II, IV
♁
♁
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19.Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first).
IV < II < I < III I < III < II < IV II < I < IV < III III < I < IV < II
20.Which is the correct structure for 2-hydroxybenzophenone?
I II III IV
21.Which is the major product from the reaction of 1,6-cyclodecanedione with hot aqueous NaOH?
I II III IV
22.Which monosaccharides have the D configuration?
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23.Which molecules are zwitterions?
I, III II, III III, IV I, IV
24.Fats, oils, phospholipids, prostaglandins and steroids have which properties in common? I) oxygen functionality
II) nonpolar groups III) rings
IV) unsaturation
III, IV I, II I, III II, IV
25.Which splitting pattern (Ha:Hb:Hc) is observed ?
doublet:triplet:doublet singlet:doublet:singlet singlet:triplet:singlet doublet:sixtet:doublet
26.Which is the index of hydrogen deficiency for a compound having molecular formula C7H5Cl2NO?
4 5 6 7
27.Which compound has an IR absorption at 3300 cm-1 but no band at 1710 cm-1?
a b c d
VIII. Answer the following questions. (12%, 4% each)
28.Draw the chemical structure of 4,6-diisopropyl-2-methylnonane.
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30.Following figure is a H-NMR spectrum for a compound that is a colorless liquid with the molecular formula C
7H14O. Propose a structural formula for the compound.
