上海交通大学试卷(B卷)
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上海交通大学试卷（B卷）
2006至2007年第1学期
班级号：____________________ 学号：__________________ 姓名：_________ 课程名称：Organic Chemistry II (Jan.26，2007)
You have 120 minutes to answer all of the following 10 questions. The total value of them is 100 points. Good Luck!
1.(5 points) In your mind, what are the five key points you learned in organic chemistry?
Why?
2.(10 points) What are the differences between aryl halides and alkyl halides in the
substitution reactions? Why?
RX : SN1 and SN2
ArX : SNAr X
EWG
addition-elimination
Elimination – addition : Bengyne
NH
2
2NH2
H Elimination
addition Explaination:
a)
No reaction SN2 Steric hindrance
+anstable no SN1
b)sp2C-X shorter and stronger
resonance
X X
3.(10 points) How about the reaction of phenol with concentrated sulfuric acid? Explain
its mechanism and performance in detail.
Answer
OH
concd
24
25度
100度
3H
OH
3H
度
Major. Under kinetic control
Major. Under thermodynamic control
Stable:
OH
3H
OH
SO3H >
Reaction Rate: OH
SO3H
OH
SO3
H
>
Machanism: electrophilic aromatic substitution
a)
2H2SO4SO3H3O HSO
4
++
b)
S O
H
O
O
OH
Stable
Other Resonace Structure c)
SO3
OH
H2SO4
+
d)
OH
+
O H
H
SO 3H
OH
+H 2O
4.(10 points) What are the named reactions as follows? (Give examples)
(a)The Diels-Alder reaction
+
(b)
The Friedel-Crafts alkylation
CH2CHClCH3
+
AlCl
(c)The Claisen condensation
2CH32H5
O
3CCHCOC
2H5
O O
Na
HCl
CH322H5
O O
+C2H5OH
(d)The Michael addition
C2H5
O
H3C
H3C
CH2
2H5
COC2H5
O
+
C2H5ONa
C2H5OH
25°
CH3C CH2C OC2H5
CH3
2C2H5)
O
5. (11 points) What is aldol reaction? Give its mechanisms in the presence of acid and base
respectively?
Answer
2CH 3O 10% NaOH,25度
CH 3CCHCH 2OH O
2-CH 3CH CH C H
O
Acid:
CH 3C
3
O
3C
2Cl
CH 3CH
2
OH
HCl
+CH 3C
2
C CH 3
H 3C C CH 2C OH
CH 33
OH
CH 3C CH C O H
O
CH 33Cl
CH 3C
CH C
CH 3
O CH
3
HCl
H 2O
+
+
Base
(a)
H
O
H 2C H
O
C H
O CH 2C H
O H 2O
enolate anion
(b)
CH 3C O CH 2C H
O CH 3CH CH 2C H
O
O
(c)
CH 3CH 2C O
H O H
CH 3CH CH 2C H
O
OH +
OH