課程名稱︰有機化學二
課程性質︰必修
課程教師︰羅禮強
開課系所︰化學系
考試時間︰June 22,2006
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試題 :
1.Which of the following two molecules do you expect to be the major product
formed when cyclopentadiene undergoes 1,2-addition with one mole of HCl?
Explain.(10 point)
Cl
Cl ∣
╱╲╱ ╱╲
\\╴/ \\╴/
2.Please construct MO energy diagrams for the cyclopropenyl cation , radical
and anion.Indicate with one(s) of the above species is aromatic according
to the Huckel's criteria.(10 point)
3.Please draw structural formula for each compound.(10 point)
(a)Triphenylmethane
(b)3,5-Dinitrotoluene
(c)1-Phenyl-2propanamine
(d)Pentachlorophenol
(e)Benzyltrimethylammonium hydroxide
4.Please describe a chemical procedure to separate a mixture of the following
two compound and to recover each in pure form.(10 point)
OH
╱╲／ ╱╲╱╲
∣O ∣ ∣O ∣ OH
╲／╲ ╲╱
CH3
5.When warmed in dilute sulfuric acid , 1-phenyl-1,2-propanediol undergoes
dehydration and rearrangement to give 2-phenylpropanal.(16 point)
(a)Propose a mechanism for this reaction.
(b)Account for the fact that 2-phenylpropanal is formed rather than its
constitutional isomer , 1-phenyl-1-propanone.
6.Using ethylbenzenes as the only aromatic starting material , show how to
synthesis the following compounds . You may use any other necessary organic
and inorganic chemicals.(14 point)
(a) ╴ (b) ╴
∕O ﹨╴≡╴H ∕O ﹨╱╲
﹨╴∕ ﹨╴∕ COOH
7.Pyrrole undergoes electrophilic aromatic substitution preferentially at the
2 position over the 3 position as illustrated by the following reaction.
Please offer an explanation for this experimental result.(14 point)
NO2
╴ CH3COOH ╴ ╴╱
// \\ + HNO3 ───→ // \\ // \\
﹨ ∕ 5'C ﹨ ∕╲ + ﹨ ∕
N N NO2 N
| | |
H H H
8.Propose a synthesis for the following compound from benzene.(14 point)
H
N
╱╲╱ ╲╱╲╱
∣O ∣ ∥
╲╱ O
｜
Cl
9.Show how to bring about each step in the following synthesis.(15 point)
OH OCH3 OCH3 OCH3 OCH3 OCH3
｜ ｜ ｜ ｜ ∣ ｜
╱╲ (a) ╱╲ (b) ╱╲ (c) ╱╲ (d) ╱╲ (e) ╱╲
｜O ｜ ─→│O │ ─→│O │ ─→│O │ ─→│O │ ─→│O │
╲╱ ╲╱ ╲╱ ╲╱ ╲╱ ╲╱
｜ ｜ ∣ ｜
NO2 NH2 CN CH2NH2
10.Propose a mechanism for the following Ritter reaction . What is the product
of a Ritter reaction using CH3CN , instead of HCN , followed by reduction
of the Ritter product with lithium aluminum hydride?(15 point)
O
╴| HCN ╴| ∥
/╲ ──→ /╲ ／╲
OH H2SO4 N H
H
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