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10.1 Organic and Inorganic
Compounds
"Organic chemistry nowadays almost
drives me mad. To me it appears like
a primeval tropical forest full of the
most remarkable things, a dreadful
endless jungle into which one does
not dare enter for there seems to be
no way out."
Friedrich Wöhler, 1835
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3–1
10.1 Organic and Inorganic
Compounds
Organic chemicals contain carbon.
It was thought that organic compounds could
only be formed in living organisms; they
required a “vital force” to be produced.
Inorganic compounds do not contain carbon
(with a few exceptions) and can be obtained
from mineral sources.
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3–2
10.1 Organic and Inorganic
Compounds
In 1828, Friedrich Wöhler produced urea from
inorganic compounds.
H
N H
H
H
1+
..
N
..
.. 1–
C O
..
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O
.. C ..
N
H N
H
H
H
3–3
10.1 Organic and Inorganic
Compounds
And then the fun began!
Synthetic Dyes: William Perkin, 1856
Carbohydrates: Emil Fischer, 1884
Aspirin: Felix Hoffmann, 1899
Plastics: Leo Baekeland, 1908
Antibiotics: Early 20th Century
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3–4
Figure 10.1 Number of known
compounds
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3–5
10.2 Bonding Characteristics of
Carbon
Carbon forms very strong bonds with itself
and other elements.
Carbon forms bonds with many geometries.
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3–6
Bond energies in kJ/mol (single bonds)
H
H
C
N
O
F
436
413
391
463
565
347
293
358
485
163
201
272
146
190
C
N
O
F
155
Other 4A: Si-Si, 222 kJ/mol; Ge-Ge, 188 kJ/mol
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3–7
Bond Geometries for Carbon
Tetrahedral:
Four single bonds (that’s a lot!)
Trigonal planar: One double bond and
two single bonds
Linear:
One triple bond and
one single bond
or
Two double bonds
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3–8
How Do We Keep Track?
Functional Groups!
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3–9
1.
2.
3.
4.
5.
Hydrocarbons (contain only C and H)
Alcohols (R–O–H, similar to H–O–H )
Carbonyls (C=O)
Carboxylic Acids
Esters (from carboxylic acids and alcohols)
R1
O
O
C
C
R2
3
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R
4
O
O
H
R1
C
O
R2
5
3–10
6. Amines (ammonia with carbon)
7. Amino acids (carboxylic acid and amine)
8. Amides (from carboxylic acid and amine)
R1
..
N R
3
R2
..
H N CH C O H
2
H
6
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O
O
7
R
C
N
H
H
8
3–11
Hydrocarbons
1. Alkanes; all carbons are tetrahedral
2. Alkenes; contain double bonds
3. Aromatics; contain alternating double and
single bonds in ring structures
H
H
H
H
H
C
H C
C H
H
C
H
H C
C
H C
C H
C
H
H
H H
H C
C
C
H
H
H H
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H
H
H
H
C
C
C
C
C
C
H
H
H
3–12
10.4 Alkanes
H
H
C
H
H
H
C
H
H
C
C
H
H
H H
2. Ethane
H
1. Methane
H
H
H
C
H
H
C
H
H
H
C
C
C
H
H
H
H
H
H
H
H
3. Propane
H
C
H
H
C
H
H
C
C
H
C
H
H
H
H
4. Butane (straight and branched chain isomers)
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10.5 Structural formulas
H
H
C
H
CH3
H
C
H
H
C
H
H
C
H
H
H
H
H
C
C
H
C
H
H
4. Butane (straight and branched cha
CH2 CH2 CH3
a. Condensed
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b. Skeletal
3–14
10.6 Structural Isomerism
Simple alkanes have formulas CxH2x+2.
More than one structure can have the formula!
C4H10
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
H
H
C
H
H
C
C
H
C
H
H
H
H
4. Butane (straight and branched chain isomers)
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3–15
10.6 Structural Isomerism
C5H12
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10.7 Conformations of Alkanes
Atoms can rotate around single bonds,
so alkanes are quite flexible!
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10.9 Cycloalkanes
Hydrocarbons in which the carbons are connected in ring structures. Formula: CxH2x
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10.12 Sources of Hydrocarbons
Petroleum (rock oil) is a mixture of hydrocarbons
found dome-shaped rock formations.
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10.12 Sources of Hydrocarbons
The mixture is separated by distillation based on
boiling points of
the hydrocarbons.
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3–20