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 addition-elimination

Elimination – addition : Bengyne

Elimination addition

Explaination:

a)

b) sp2C-X shorter and stronger

resonance

3.

(10 points) How about the reaction of phenol with concentrated sulfuric acid? Explain its mechanism and performance in detail.

Answer

Machanism: electrophilic aromatic substitution

a)

b)

c)

d)

4.

(10 points) What are the named reactions as follows? (Give examples)

(a) The Diels-Alder reaction

(b) The Friedel-Crafts alkylation

(c) The Claisen condensation

(d) The Michael addition

5.

(11 points) What is aldol reaction? Give its mechanisms in the presence of acid and base respectively?

Answer

Acid:

Base

(a)

(b)

(c)

6.

(10 points) Outline a route to prepare the following compound from benzene and other needed reagents:

Answer

7.

(10 points) Preparation of the following compound from ethylene.

Answer

8.

(9 points) Give three different methods for converting carbonyl groups of aldehydes and ketones to –CH2- groups.

answer

a) The Clemmensen Reduction

b)

c) Wolff-Kishner reduction

9.

(15 points) Explain the following items using examples:

(a) Markovnikov addition vs anti-Markovnikov addition

(b) Zaitev rule vs. Hofmann rule

(c) Oxidation vs reduction

Answer

a) Markovnikov addition

Anti- Markovnikov addition

b) Zaitev rule

To form the more stable alkene

Hofmann rules

To form the least substituted alkene

c) Oxidation : to increase its oxygen content (decrease its H content) or its content of any element more electronegative than cabon.

Reduction : the opposite of oxidation

10.

(10 points) Describe the impotance and limitations of Grinard reagents in organic synthesis.

Answer

Limitations: sensitive to H2O and –OH, -NH2, -NHR, -COOH, -SO3H, -SH, -CH (acid)

and

上海交通大学试卷（B卷）