課程名稱︰有機化學一
課程性質︰化學系必修
課程教師︰羅禮強
開課學院：理學院
開課系所︰化學系
考試日期（年月日）︰2012/1/12
考試時限（分鐘）：110分鐘
是否需發放獎勵金：是
（如未明確表示，則不予發放）
試題 :
1. Please name the following species or groups. (9 points)
(a) (b) (c) (d) (e)
Br OH HO OH
+ ｜ ｜ - ｜ ｜
—Ｃ— —Ｃ—Ｃ— —Ｃ≡Ｃ: —ＣＨ2— —Ｃ—Ｃ—
｜ ｜ ｜ ｜ ∣
(f)
+
—Ｏ—
︱
2. Please name the following compounds. (12 points)
(a) (b) (c) (d)
Ｏ
∥ ╱＼／＼
H3C—Ｓ—Cl ∣Ｏ｜ OH SOCl2 CH2N2
∥ ＼／
Ｏ
(e) (f) (g) (h)
OCH3
｜ ｜ ◥ OsO4 (CH3CH2CH2)3B
／＼ ╱╲ ╱╲╱╲╱╲
O
3. Predict the intermediates and final product(s) obtained when (2R,3R)-
2-bromo-3-methylpentane is subjected to the following sequence of
reactions, briefly explaining your rationale. Provide regiochemical and
stereochemical details as relevant.
NaOC2H5/C2H5OH, heat; (b) BH3, THF; (c)H2O2, OH-. (6 points)
4. Draw Fischer projection formula(s) of the major product(s) pf the reaction
between (E)-3-hexene and aqueous Br2. (4 points)
5. Draw Fischer projection formula(s) of the major product(s) of the reaction
between (Z)-2-butene and cold, alkaline KMnO4. (4 points)
1 13
6. Provide the predicted H-and C-NMR spectra for the following compounds.
Provide explanation for your answers. (20 points)
(a) (b) Ｏ
╲╱╲╱ ╲
CH3CH2CH2Br ∥
Ｏ
7. Provide a mechanistic explanation for the following observation: The same
major product is obtained when 2-ethyl-1-hexene and 3-methyl-2-heptene are
allowed to react with HCl. (5 points)
13
8. Explain why the signal of CDCl3 appears as a triplet in a C-NMR spectrum.
(4 points)
9. Complete the following reaction sequence: indicate regiochemical/
stereochemical details as relevant. (6 points)
i) Br2, hv
ii) C2H5ONa/C2H5OH, heat
1,1,2-trimethylcyclohexane -----------------------------> ？
iii) Ozonolysis
10. Draw bond-line formula (including stereochemistry) of all monochloro
derivatives that might be formed when 2,3-dimethylbutane is allowed to
react with Cl2 under UV irradiation. (4 points)
13
11. Interpret the following C-NMR spectrum of a compound C5H10Br2: elucidate
13
the structure and assign all the C resonances. DEPT experiments indicate
that all the three signals are CH2. (6 points)
││
││
││ │
╨────────────────┴┴─┴────────
─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─
75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 ppm
12. Write structural formulas for the following compounds. (6 points)
1
C5H10O: H-NMR δ2.50 (m,1H), 2.10(s,3H), 1.10(d,6H);IR:strong peak near
1720 cm-1. (s:singlet, d:doublet, t:triplet, q:quartet, m:multiplet)
13. Provide a reasonable synthetic strategy for the synthesis of the following
compound. You may use any compounds containing THREE carbons or fewer as
the starting material. (8 points)
╱╲ + enantiomer
◢￣￣◣╱╲
14. Write a radical chain reaction mechanism for the following reaction.
(6 points)
Ｏ
∥ Br Br
╱＼╱╲ ╱ heat ╱＼╱
｜ ∣ Ｏ ------> ∣ ｜ + CO2
＼╱ ＼╱
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