copyright © houghton mifflin company. all rights reserved.3–13–1 10.1 organic and inorganic...

Copyright © Houghton Mifflin Company. All rights reserved. 3–1

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



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.



In 1828, Friedrich Wöhler produced urea from inorganic compounds.

N

H

HH

H

1+

N C O....

..

..1–

C

O

NN

H HH H

.. ..



And then the fun began!

Synthetic Dyes: William Perkin, 1856Carbohydrates: Emil Fischer, 1884Aspirin: Felix Hoffmann, 1899Plastics: Leo Baekeland, 1908Antibiotics: Early 20th Century


Figure 10.1 Number of known compounds


10.2 Bonding Characteristics of Carbon

Carbon forms very strong bonds with itself and other elements.

Carbon forms bonds with many geometries.


Bond energies in kJ/mol (single bonds)

Other 4A: Si-Si, 222 kJ/mol; Ge-Ge, 188 kJ/mol

H C N O F

H 436 413 391 463 565

C 347 293 358 485

N 163 201 272

O 146 190

F 155


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


How Do We Keep Track?

Functional Groups!


1. Hydrocarbons (contain only C and H)

2. Alcohols (R–O–H, similar to H–O–H )

3. Carbonyls (C=O)

4. Carboxylic Acids

5. Esters (from carboxylic acids and alcohols)

3 4 5

C

O

R1 R2

C

O

OH

RC

O

OR1

R2


6. Amines (ammonia with carbon)7. Amino acids (carboxylic acid and amine)8. Amides (from carboxylic acid and amine)

6 7 8

N

R1 R2

R3

..

CCH2

O

OHNH

H

..C

O

N

H

HR


Hydrocarbons

1. Alkanes; all carbons are tetrahedral

2. Alkenes; contain double bonds

3. Aromatics; contain alternating double and single bonds in ring structures

C

CC

C

CC

H HHH

HH

HH

HH

HH C

CC

C

CC

H H

HH

HH

HH

H

H

C

CC

C

CC

H

H

H

H

H

H


10.4 Alkanes C

H

HH

H

C C

H

H

H

H

H

H

C C CH

H

H

H

H

H

H

H

1. Methane 2. Ethane 3. Propane C C C C

H

H

H H

H

H

H

H

H

HC

H

CC

C

H H

HHH

H

H H

H

4. Butane (straight and branched chain isomers)


10.5 Structural formulas C C C C

H

H

H H

H

H

H

H

H

HC

H

CC

C

H H

HHH

H

H H

H

4. Butane (straight and branched chain isomers) CH3 CH2 CH2 CH3

a. Condensed b. Skeletal


10.6 Structural Isomerism

Simple alkanes have formulas CxH2x+2.

More than one structure can have the formula!

C4H10 C C C C

H

H

H H

H

H

H

H

H

HC

H

CC

C

H H

HHH

H

H H

H

4. Butane (straight and branched chain isomers)


10.6 Structural Isomerism

C5H12


10.7 Conformations of Alkanes

Atoms can rotate around single bonds, so alkanes are quite flexible!


10.9 Cycloalkanes

Hydrocarbons in which the carbons are con-nected in ring structures. Formula: CxH2x


10.12 Sources of Hydrocarbons

Petroleum (rock oil) is a mixture of hydrocarbons found dome-shaped rock formations.


10.12 Sources of Hydrocarbons

The mixture is sep-arated by distil-lation based on boiling points of the hydrocarbons.

copyright © houghton mifflin company. all rights reserved.3–13–1 10.1 organic and inorganic...

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