課程名稱︰有機化學乙上
課程性質︰必帶
課程教師︰陳昭岑
開課學院：工
開課系所︰化學工程學系
考試日期（年月日）︰101/10/18
考試時限（分鐘）：110 mins
是否需發放獎勵金：是
（如未明確表示，則不予發放）
試題 :
紅色代表凸出紙面，綠色代表凹入紙面
I. Simple Choice ( 3 points each )
1. What is the IUPAC name for the following compound?
／＼／＼／＼
∣ ∣
／＼ ＼
(A) 3-isopropyl-5-ethylheptane (B) 2-methyl-3-ethyl-5-ethylheptane
(C) 3,5-diethyl-2-methylheptane (D) 2-methyl-3,5-diethylheptane
2. Which of the following compounds are constitutional isomers?
∣ ∣ ∣ ∣
＼／＼ ＼／＼ ＼／＼ ＼／＼
∣ ∣ ∣ ∣ ∣
／＼／＼／＼／＼ ／＼／＼／＼／＼ ／＼／＼／＼／ ＼／＼／＼／
∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣
／＼
A. B. C. D.
(A) A and C (B) B and D (C) C and D (D) A and D
3. Which of the following is a wedge and dash projection for the following
Newman projection?
H Cl H H Cl
＼ ∣ ／ ＼ ∣ ／ ＼ ∣ ／ ＼ ∣ ／
∣ ╭∣╮ ╭│╮ ╭∣╮ ╭∣╮
／＼／ │∣│ │││ ∣∣∣ ∣∣∣
∣ ／┬＼ ／┬＼ ／┬＼ ／┬＼
Cl ↖ ／ │ ＼ ／ ∣ ＼ ／ ∣ ＼ ／ ∣ ＼
Cl H Cl H H
(A) (B) (C) (D)
4. Which of the following is the most stable isomer?
(A) ∣ (B) ∣ (C) ∣ (D) ∣
／＼／ ／＼／ ／＼／ ／＼／
∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣
＼／ ＼／ ＼／ ＼／
∣ ∣ ∣ ∣
／＼ ／＼ ／＼ ／＼
5. Identify the most acidic proton on the following compound.
Hc
Ha ／
∣ ∥
＼／＼／＼／＼／＼
∣ Hd
Hb
(A) Ha (B) Hb (C) Hc (D) Hd
6. The basic species are arranged in decreasing order of basicity in the
sequence:
(A) F- > -OCH3 > -NH2 > CH3CH2- (B) -OCH3 > CH3CH2- > -NH2 > F-
(C) CH3CH2- > -NH2 > -OCH3 > F- (D) -NH2 > CH3CH2- > F- > -OCH3
7. Which of the following reaction does not proceed?
(A) CH3Li + CH3CH2OH ─→ CH4 + CH3CH2OLi
(B) HC≡CH + NaOH ─→ HC≡CNa + H2O
(C) HC≡CNa + H2O ─→ HC≡CH + NaOH
(D) CH3OH + NaH ─→ CH3ONa + H2
8. Which of the following molecules, with any formal charges omitted, would
be considered the most likely Lewis structure for nitric acid, HNO3?
.. .. .. ..
Ｏ: :Ｏ Ｏ: .. Ｏ:
∥ .. ..＼..／.. Ｈ :Ｏ: ∥
Ｈ Ｎ＝Ｏ: Ｎ ＼ ∣ Ｈ Ｎ
＼ ／ ∥ Ｎ＝Ｏ ＼ ／ ＼..
:Ｏ Ｏ: .. ＼.. :Ｏ Ｏ:
.. ／.. Ｏ: .. ..
Ｈ ..
I II III IV
(A) I (B) II (C) III (D) IV
9. For a bond forming reaction involving donation of electrons between atoms,
electron density is transferred into which molecular orbital of the
accepting atom?
(A) σ orbital (B) p orbital (C) s orbital (D) LUMO
10. Which of the following statement is CORRECT description for the structure
shown below?
Cl Cl
＼／＼／
∣ ∣
＼／＼／＼
／＼ ∣ Cl
Cl
(A) Compound 5,8-bis(1-methylethyl)dodecane has 2 tertiary Hydrogens.
(B) Compound 4-(1-ethylpropyl)-2,3,5-trimethylnonane has 5 tertiary
Hydrogens.
(C) Compound 2,6,6-trimethylbicyclo[3,1,1]hepta-2-ene has 3 secondary
Hydrogens.
(D) The most stable structure of
2,3,4,6-tetrachloro-1-tert-butylcyclohexane shown below has 4 chlorine
atoms at the equatorial positions.
11. Of the following molecules, which is expected to have the highest melting
point?
∣ ＼／ ∣
／＼／ ／＼／＼ ／＼ ／＼
I II III IV
(A) I (B) II (C) III (D) IV
12. Which of the following statements best describes the carbon-chlorine bond
of the molecule below?
..
H :Cl:
＼ ／
H Ｃ H
＼ ／ ＼ ／
Ｃ Ｃ
／＼ ／＼
H H H H
(A) nonpolar / no dipole (B) polar / δ+ at carbon and δ- at chlorine
(C) polar / δ- at carbon and δ+ at chlorine (D) ionic
II. What is the IUPAC name for the following compounds ( 3 points each )
／＼／＼ ∣ ＼／ ／
／ │ ＼ ／＼／＼ ／＼ ∣
＼ ∣ ／￣￣ \＿/▽ ／＼／＼
＼／＼／ ∣ ╳＿∕
／ ＼／
(a) ／ (10個C) (b) (14個C) (c) (14個C)
P.S.因為圖有點難畫所以解釋一下，基本上碳都在頂點上
III. Explain the following terms concisely ( 3 points each ):
(A) Leveling effect (B) Frontier orbitals (C) Electrophile / Nucleophile
(D) Solvation (E) Polarizability
IV. What is the energy difference between the staggered and eclipsed
conformations of 2,2-dimethylpropane if the eclipsing cost of Me and H is
6 kJ/mol? ( 6 points ) Please note each hydrogen-hydrogen eclipsing
interaction in ethane costs about 4.0 kJ/mol.
V. Sketch the molecular orbitals for acetylene (10 points ).
VI. By viewing from C2-C3 axis, draw Newman projections for the two eclipsed
and two staggered conformational isomers of 2-methylbutane. Indicate the
one has the highest energy and the one has the lowest energy ( 8 points ).
VII. For each of the following resonance hybrids, rank the contributing
restructures in order of their relative importance (6 points ).
a) .. -
:Ｏ: :Ｏ:
∥ .. │ +
Ｈ─Ｃ─ＮＨ2 ←──→ Ｈ─Ｃ＝ＮＨ2
b) .. .. - .. +
Ｏ: :Ｏ: Ｏ:
∥ + │ - │
Ｈ2Ｃ＝ＣＨ─ＣＨ ←→ Ｈ2Ｃ─ＣＨ＝ＣＨ ←→ ＣＨ2─ＣＨ＝ＣＨ
c)
+ .. - ..- +
Ｈ3Ｃ─Ｎ≡Ｃ─Ｏ: ←──→ Ｈ3Ｃ─Ｎ─Ｃ≡Ｏ:
.. ..
VIII. Supply the curved arrows necessary for the following reactions.
( 6 points )
(A) ..- ..
:Ｏ: Ｏ:
∣ .. ∥ -..
Ｈ─Ｃ─Ｏ─Ｈ ──→ Ｈ─Ｃ + :Ｏ─ＣＨ3
│ .. ＼.. ..
:Ｏ Ｏ─Ｈ
..＼ ..
ＣＨ3
(B)
CH3 CH3
..- │ .. │ ..- H H
Ｈ─Ｏ: + Ｈ─ＣＨ2─Ｃ─Cl: ─→ Ｈ2Ｃ＝Ｃ + :Cl: + ＼..／
.. │ .. │ .. Ｏ
CH3 CH3 ..
IX. Draw the most stable chair conformation of glucose and a chemical
structure for 1-cyclopropyl-3-methylcyclopentane, respectively
( 6 points ).
OH
／
OH ∣
＼／＼O
∣ ∣
／＼／＼
OH ∣ OH
OH Glucose
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