organic chemistry 2 -...

Organic Chemistry 2

سید مرتضی مهرداد

گروه شیمی –دانشکده علوم پایه

به نام خدا

1. Carey, Organic Chemistry, 6th ed., McGraw-Hill, NY, 2006.

2. Carey and Sundberg, Advanced Organic Chemistry: Structure and Mechanisms

(Part A), 4th ed., Springer, 2004.

3. Carey and Sundberg, Advanced Organic Chemistry: Structure and Mechanisms

(Part B), 4th ed., Springer, 2001.

4. House, Modern Synthetic Reactions, 2nd ed., W. A. Benjamin, New York, 1972.

5. Lowry and Richardson, Mechanism and Theory in Organic Chemistry, 3rd ed.,

Harper and Row, New York, 1987.

6. McMurry, Organic Chemistry, 6th ed., Brooks/Cole, Monterey CA, 2003.

7. Morrison, Boyd and Boyd, Organic Chemistry, 6th ed., Benjamin Cummings, CA,

1992.

8. Solomons and Fryhle, Organic Chemistry, 8th ed., Wiley, NY, 2003.

9. Streitwieser, Heathcock, and Kosower, Introduction to Organic Chemistry, 4th ed.;

Prentice-Hall, Saddle River, NJ, 1998.

10. Sykes, A Guidebook to Mechanism in Organic Chemistry, 6th ed., Longmans

Scientific and Technical, Essex, 1986.

11. Vollhardt and Schore, Organic Chemistry, 4th ed.,W.H. Freeman, New York,

2002.

نمره25: کوئیز

نمره15: نظم و ترتیب و حضور و غیاب

نمره60: امتحان نیم ترم

نمره100: امتحان آخر ترم

1992

احمد میرشکرائی -عیسی یاوری -علی سیدی اصفهانی: ترجمه

1372تهران -نشر علوم دانشگاهی

Aromaticity

Benzene

14.1

Organic Compounds

Aliphatic Compounds (fatty)

Aromatic Compounds (fragrant)

14.2

Benzene has been known since 1825

In spite of this, no satisfactory structure for benzene had been advanced

until about 1931

14.3

14.3

1858(chain) 1865(ring)

II, III & V

1867

(rapid equilibrium Could not be separated)

14.4

14.1

14.1

14.5

The quantity of heat

evolved when one mole of

an unsaturated compound is

hydrogenated

14.6

14.7

H3C CH3

1.53Ao

C C

1.34Ao 1.39Ao

1.48Ao

14.8

14.2 14.2

14.3

14.3

14.9

14.10

the p clouds must contain a total of (4n + 2) p electrons

Benzene

6 electrons

Aromatic sextet 4n + 2 = 6

n = 1

Cyclopentadiene Unusually strong acid

Ka = 10-15

H

H

H

H

H H

H

H

H

H

H

H

H

H

Cycloheptatriene Ka = 10-45

.

.

14.5

Br-

p-complexes

Name of substituent group + benzene 14.11

Name the two group successively + benzene

or a derivative of the special name of molecule

Numbers are used to indicate their relative positions

14.12 Polynuclear aromatic hydrocarbons - Naphthalene

14.8

Diamond Graphite

buckminsterfullerene

20

12

14.13

nitrogen

- Dumas method

- Kjeldal method

sulfur - Carius method