‫به نام خدا‬
‫‪Organic Chemistry 2‬‬
‫سید مرتضی مهرداد‬
‫دانشکده علوم پایه – گروه شیمی‬
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.
‫کوئیز‪25 :‬نمره‬
‫نظم و ترتیب و حضور و غیاب‪15 :‬نمره‬
‫امتحان نیم ترم‪60 :‬نمره‬
‫امتحان آخر ترم‪100 :‬نمره‬
‫‪1992‬‬
‫ترجمه‪ :‬علی سیدی اصفهانی‪ -‬عیسی یاوری‪ -‬احمد میرشکرائی‬
‫نشر علوم دانشگاهی ‪ -‬تهران ‪1372‬‬
Aromaticity
Benzene
14.1
Aliphatic Compounds (fatty)
Organic Compounds
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
14.5
The quantity of heat
evolved when one mole of
an unsaturated compound is
hydrogenated
14.1
14.6
H3 C
CH3
1.53A
14.7
o
C
C
1.34Ao
1.48Ao
1.39Ao
14.8
14.2
14.3
14.3
14.9
14.10
the p clouds must contain a total of (4n + 2) p electrons
4n + 2 = 6
n=1
Aromatic sextet
Benzene
6 electrons
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Cyclopentadiene
Cycloheptatriene
Unusually strong acid
Ka = 10-15
Ka = 10-45
.
.
Br-
p-complexes
14.5
14.11
Name of substituent group + benzene
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
Graphite
Diamond
buckminsterfullerene
20
12
14.13
- Dumas method
nitrogen
- Kjeldal method
sulfur
- Carius method