1. Organic

2. Introduction
Two Group 14 elements, carbon and silicon, form the basis for most natural substances.
Silicon, with its great affinity for oxygen, forms chains and rings containing Si-O-Si bridges to produce silica and silicates that form the basis for most rocks, sands, and soils. Silicon may be the most important element in the geological world.

3. Carbon
Carbon has the unusual ability of bonding to itself to form long chains or rings of carbon atoms.
Carbon forms strong bonds to other nonmetals such as hydrogen, nitrogen, oxygen, sulfur, and the halogens.
Several million (11 million-plus) are known, and the number continues to grow rapidly.
Carbon is the most important compound to the biological world.

4. Organic Chemistry
Organic Chemistry is the study of carbon-containing compounds and their properties.
Oxides and carbonates that contain carbon are not considered to be organic, they are inorganic.
The original distinction between organic and inorganic was based on whether a compound was produced by living things.
Organic chemistry plays a vital role in our quest to understand living systems.

5. Industrial organic chemistry produces synthetic fibers (nylon, rayon), plastics, rubber (latex) explosives, artificial sweeteners, vinegar and pharmaceuticals that are such an important part of modern life.
The energy on which we rely so heavily on to power our civilization is based mostly on organic materials found in coal and petroleum.

6. Saturated and Unsaturated Hydrocarbons
Hydrocarbons are compounds composed of carbon and hydrogen.
Saturated hydrocarbons contain carbon-carbon bonds that are all single bonds (each carbon is bonded to four atoms).
Unsaturated hydrocarbons contain carbon-carbon multiple bonds and can react with additional atoms.

7. Hydrocarbons Saturated means it is “full of hydrogen”
Unsaturated is “missing hydrogens” because of the double/triple bonds.
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8. Root words # of C atoms Meth 1 Hex 6 Eth 2 Hept 7 Prop 3 Oct 8 But 4
Non 9
Pent 5
Dec 10

9. So for example H H H H H-C-C-C-C-H H H H H H H H H H H H H
H-C-C-C-C-C-C-C-C-H
butane
H H H H H H H H
octane
H H H H
H-C-H
H-C-C-C-H
H H H
propane
methane

10. Molecular Formulas Alkanes always have the molecular formula of:
CxH2x+2
2 H on every C except the end, they get 3
Hexane-
C6H14 molecular formula
H H H H H H
Lewis Dot, or
Structural Formula
H-C-C-C-C-C-C-H
H H H H H H

11. Skeleton Formulas
Drawing Lewis Dot structural formulas for long organic compounds can get rather tedious.
So organic has shortened it
They don’t write the C’s or the H’s
You draw a jagged line, at each corner there is a Carbon
Assume all extra spaces are filled with H

12. For Example H H H H H H H H-C-C-C-C-C-C-C-H H H H H H H H
Heptane, C7H16
H H H H H H H =
H-C-C-C-C-C-C-C-H
H H H H H H H
Nonane, C9H20
H H H H H H H H H =
H-C-C-C-C-C-C-C-C-C-H
H H H H H H H H H

13. Isomers
Isomers- compounds with the same molecular formula but different structural formulas
Different structural formulas mean it has different properties
Butane is the first alkane with a possible isomer
H H H H =
H-C-C-C-C-H
H H H H
H H H or
H-C- C - C-H
H HCH H
Both are C4H10 H

14. Butane
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15. Naming Isomers Name the longest chain possible.
As a prefix name the chain attached with –yl on the end and give the number of the carbon atom it is attached to 6 4 2 3 1
Longest Chain 5 7 3
ethyl
heptane
It could also be 5 ethyl heptane if you started numbering from the other side, when given an option always go with the Lower number!!!

16. Name this molecule And give its molecular formula 4 ethyl octane
C10H22
4 propyl decane
C13H28

17. Cyclic Hydrocarbons C4H8
A hydrocarbon that is a ring instead of a chain. To name it, give it the prefix “cyclo-”
Molecular Formula
Subtract 2 H from CxH2x+2
CxH2X
cyclobutane
C4H8
H H
H-C-C-H
H-C-C-H
H H

18. Name the following compounds and give their formula
cycloheptane
cyclohexane
C7H14
C6H12
cyclooctane
cyclodecane
C8H16
C10H20

19. Name and give the formula
Methyl cyclohexane
C7H14

20. Alkenes Contain a double bond
They get the suffix “-ene” and the number of the carbon atom the double bond is on (lowest number)
Molecular formula
Subtract 2 H for each double bond from CxH2x+2
Skeleton fomula
1 butene
H H H
H-C=C-C-C-H
C4H8
H H H

21. Alkynes H-C-C=C-C-C-H Skeleton fomula 2 pentyne H H H H H H
Contain a triple bond
They get the suffix “-yne” and the number of the carbon atom the triple bond is on. Molecular formula
subtract 4 H for each triple bond from CxH2x+2
Skeleton fomula
2 pentyne
H H H
H-C-C=C-C-C-H
H H H
C5H8

22. Name and give the formula for these compounds
2 hexene
C6H12
Cyclopentane
C5H10
3 methyl nonane
C10H22
ethyne (commonly known as acetylene)
C2H2
3 methyl 1 pentene
C6H12

23. Name and give the formula for these compounds
2 heptene
C7H14
Cyclopentene
C5H8
cyclopropane
C3H6
1 butyne
C4H6
3 ethyl 1 hexene
C8H16

24. Doubles and triples
If you have two of the same thing put “di” in front of it
If you have three of the same thing put “tri” in front of it

25. Examples
2,3 hexadiene
C6H10
3,4,4 trimethyl heptane
C10H22

26. Multiple groups on a chain
Name each and put them in alphabetical order
3, 4 diethyl 2 methyl
1 heptene
C12H24

27. Common functional groups

28. Functional Groups
Atoms other than hydrogen or carbon covalently bonded to a carbon atom in an organic molecule.
Most commonly oxygen, nitrogen, or the halogens.
The presence of a functional group drastically changes the chemical properties of a molecule.

29. Different Functional groups with a 2 carbon chain
Ethane- gas (found in natural gas)
Ethanol- grain alcohol (drinkable)
Ethanoic acid- vinegar
Diethyl ether- starting fluid
Chloro fluoro ethane (CFC’s used as refrigerants)
Ethanal- foul smelling liquid (similar to formaldehyde)

30. Halogenated Hydrocarbons
Hydrocarbons with halogens attached
Before the main chain name the halogen as either fluoro, chloro, bromo or iodo and give its number
For each halogen subtract 1 H Cl
1,3-dichloro cycloctane
C8H14Cl2 Cl

31. Practice 2 fluoro 1 butene C4H7F 2,5-dibromo 3-ethyl 4-methyl heptane
C10H20Br2

32. Alcohols Hydrocarbons with an –OH attached
To name it, give it the suffix –(an)ol and the number the OH is attached to
Normally you subtract one H from the main group and put an OH on the end (to signify it is an alcohol)
2 propanol
Commonly
Isopropanol or
Rubbing alcohol H O
C2H5OH
Ethanol
C3H7OH OH

33. Aldehydes Hydrocarbons with a =O on the outer edge of the chain
(most have a foul stench, like formaldehyde or methanal)
To name it add the suffix “–al”
For the formula subtract 2 H and add O =O O=
octanal
hexanal
C8H16O
C6H12O

34. Ketones Hydrocarbons with a =O not on the edge of the compound
To name it add the suffix “–one”
For the formula subtract 2 H and add O O=
cyclopropanone
C3H4O O=
C9H18O
3-nonanone

35. Carboxylic Acid Hydrocarbons with a –COOH group attached
To name it give it the suffix “–oic acid”, the C in the group does count
Subtract one C one H and add COOH
This group looks like…
Pentanoic acid
R-C=O
C4H9COOH O H =O O H

36. Everything so far… *R means any carbon chain Alcohols Carboxylic Acids
Alkanes, alkenes, and alkynes
Isomers, halogenated and cyclic
*R means any carbon chain
Alcohols
Carboxylic Acids
R-OH
R-C=O
-ol
-OH
-oic acid
Aldehydes
Ketones
on the end
R-C-R
R=O =O
-one
-al

37. Predicting organic reactions
Addition reactions occur by adding halogens or hydrogen to alkene or alkynes.
In the reaction, the new molecule takes the place of the double or triple bond.
Cl2 + CH3-CH=CH2  CH3-CClH- CClH2

38. example
1- butene is reacted with fluorine
C4 H8 + F2  C4H8F2

39. Predicting organic reactions
Substitution reactions occur by adding halogens to an alkane.
In the reaction, the new molecule takes the place of a hydrogen.
Cl2 + CH3-CH3  CH3-CClH2 + HCl
Cl2 + C2H6  C2ClH5 + HCl

40. Predicting organic reactions
Combustion reactions occur when an organic compound is burned in oxygen.
The products of a complete combustion are water vapor and carbon dioxide.
C6H12O6 + 6 O2  6 H2O+ 6 CO2

41. Predicting organic reactions
Esterification reactions
Made by reacting carboxylic acids with alcohols.
R-C-O-H
H-O-R O= +
R-C-O-R O=
+ H-O-H
Carboxylic acid
alcohol
Ester

42. Examples Fluorine is added to 1 propene Ethanol is burned in oxygen
Chlorine is added to propane
Ethanoic acid is reacted with 1-butanol

43. What is petroleum? Also known as crude oil It is a thick black sludge
It comes from ancient plant and animal life long since buried and kept under extreme pressure for millions of years.
It is composed of countless different organic compounds.

44. What is made from petroleum
Gasoline, kerosene, and rocket fuel
Most plastics and other polymers (elastomers and fibers)
Synthetic rubbers and fabrics
Most pharmaceutical drugs
And several other things
If we run out of petroleum it would have a devastating effect on us

45. One compound that comes from petroleum
Benzene
Which has the resonance structure
It also is drawn as

46. Compounds that contain benzene are called aromatic
Aspirin (acetyl salicylic acid)
O-H O O= O

47. Compounds that contain benzene are called aromatic
Trinitro Toluene (TNT)
O2N-
- NO2
O2N-

48. A few other aromatics
Vinyl, napthalene (found in moth balls), acetaminophen, penacillin
Benzene is an extremely common organic compound
The fact that the double bonds flip back and forth (called resonance) give it a very stable structure

49. Polymerization

50. Esters
Esters- a functional group in the middle of a carbon chain; R-COO-R
It gets the suffix –oate
It is very similar to carboxylic acids
~In fact, it is formed by a
carboxylic acid and an alcohol
R-C-O-R O=
R-C-O-H
H-O-R + O=
R-C-O-R
+ H-O-H
the water came
from… O=

51. Now if you have a few compounds that have both a
Carboxylic acid end
+ H-O-H
+an alcohol end
H-O-
R-C-O-
R-C-O-H
H-O-
R-C-O-H
H-O-
R-C-O-H + O= O= O= O=
They could form an ester that looks like…
But the compound still has a…
Carboxylic acid end
And an alcohol end
So it could repeat this process thousands even millions of times and make a whole bunch of…
esters
poly
Of course, the scientific prefix for “whole bunch of” is

52. This is the basis for a polymer
Polymer-A large chain-like molecule composed of smaller molecules linked together
The smaller units it is made up of are called monomers
monomers need to have ends that can join together (or stack on top of one another)
Like an extension cord or markers
So you could (infinitely) join them together to make a large polymer

53. Polymers can get very large
common polymers have a molecular mass of around 50,000 g/mol
The first molecules seen under a microscope were polymer chains
Common polymers include things like…
Nylon, Kevlar©, latex, PVC, rubber, acrylic, vinyl, Deoxyribonucleic acid (DNA) and carbohydrates

54. Piece of DNA

55. Polymers are put into three classes
Plastics
Fibers
Elastomers-
Polymers that can
stretch and flex
more than fibers
but less than
Elastomers
Polymers that can be
stretched to 10x their
normal size and
return to their
original shape
Polymers that
cannot stretch
or be reshaped
once formed
Polypropylene
polystyrene
and PVC
(polyvinyl chloride)
Nylon and
Acrylic
Elastic