Organic Chemistry

1
Chapter 26

• Organic Chemistry
• (Functional Groups)

2
Organic Chemistry

• Organic Chemistry
• The chemistry of Carbon compounds

3
Organic Substituents

• Alkyl Halide
• Groups other than carbon like halogens (Halo-
  group) attached to carbon chains

2,2,3 tribromopentane
4
Organic Substituents

• Aryl Halide
• Groups other than carbon like halogens (Halo-
  group) attached to arene ring like benzene.

1,2-difluorobenzene
or
ortho-difluorobenzene
5
Organic Chemistry

• Functional Groups
• When organic compounds contain Oxygen or
  Nitrogen, the result is a certain function
  (chemical characteristic) for the molecule.

6
Functional Groups

• How do you find a functional group?
• Look for oxygen or nitrogen in the organic
  molecule.

7
Functional Groups

• Alcohol Group
• OH attached to a carbon chain
• R-O-H
• The R refers to the Rest of the molecule.

General Equation
8
Hydrocarbon Prefixes
IUPAC International Union of Pure and Applied
Chemistry Hydrocarbon prefixes meth C eth C-C pro
p C-C-C but C-C-C-C Pent C-C-C-C-C hex C-C-C-C-C-C
hept C-C-C-C-C-C-C oct C-C-C-C-C-C-C-C non C-C-C-
C-C-C-C-C-C dec C-C-C-C-C-C-C-C-C-C
9
Last part of name
Alcohol Group R-OH
__________ol
methanol
methane
C
C
also called (methyl alcohol)
Can also be shown as
10
Last part of name
Alcohol Group R-OH
__________ol
ethyl alcohol ethanol
ethane
C
C
C
C
11
Last part of name
Alcohol Group R-OH
__________ol
1-propanol
C
C
C
Primary alcohol
12
Last part of name
Alcohol Group R-O-H
__________ol
1-propanol
2-propanol or Isopropyl alcohol rubbing alcohol
Primary alcohol
Secondary alcohol
13
Carboxylic Acid
___________oic acid
R
methane
methanoic acid
C
H
14
Carboxylic Acid
___________oic acid
R
ethane
ethanoic acid
C
C
C
15
Aldehyde
___________al
R
methane
methanal
C
H
formaldehyde
16
Aldehyde
___________al
R
ethane
ethanal
C
C
C
17
Ketone
___________one
R
R
propane
2-propanone
C
C
C
C
C
C
Acetone (fingernail polish remover)
18
Ketone
___________one
R
R
2-hexanone
Hexane
C
C
C
C
C
C
19
Ketone
___________one
R
R
3-hexanone
Hexane
C
C
C
C
C
C
20
Ether
___________ether
R
R
methane
dimethyl ether
O
H
C
21
Ether
___________ether
R
R
diethyl ether
O
H
C
C
22
Ester
___________oate
R
R
ethanoic acid
ethanol
O
O
H
C
C

?
C
Carboxylic Acid
Alcohol ?
Ester
water
O
H

ethyl
ethanoate
23
Alcohol (Revisited)
___________ol
H
Primary alcohol
R
C
O
H
H
R
Secondary alcohol
C
H
O
H
R
R
R
Tertiary alcohol
C
O
H
R
24
Nitro group -NO2
Nitro
R
Halide group -F -Cl -Br -I
Fluoro
R
F
Chloro
R
Cl
Bromo
R
Br
Iodo
R
I
25
Amine
___________ine
Primary amine
R
Secondary amine
R
R
R
R
Tertiary amine
R
26
Amide
___________ide
Primary amide
R
Secondary amide
R
R
R
R
Tertiary amide
R
27
Chapter 26

• Organic Chemistry
• (Polymers)

28
Organic Chemistry

• Petrochemicals
• Compounds built from oil or natural gas.
  Synthetic
• Examples Detergents, pesticides,
  pharmaceuticals, cosmetics.
• Petrochemicals are also important starting
  materials for the production of Plastics.
• Plastics Paints, fabrics, rubber, insulation
  materials, foams, glasslike substances,
  adhesives, molding and structural materials.

29
Organic Chemistry

• Ethene One of the most important builder
  molecules for plastic polymers.
• Commonly known as Ethylene.
• Its double bond makes it highly reactive.

30
Organic Chemistry

• Addition Reaction
• Production of Ethanol from Ethene.

?

Ethene
water
Ethanol
?

31
Organic Chemistry

• Addition Reaction
• Production of Ethanol from Ethene.

32
Organic Chemistry

• Monomer
• A small molecule that is the starting molecule
  for the formation of a polymer.
• Monomers generally contain double bonds that
  break to form long chain-like structures called
  polymers.
• Polymer
• An extremely large molecule, (usually 500-20,000
  or more repeating units), made by linking
  monomers together.

33
Organic Chemistry

• Low Density Polymer
• Carbon polymer chains with many branches that can
  move easily over each other.
• (Saran wrap, plastic bags)

34
Organic Chemistry

• High Density Polymer
• Carbon polymer chains that are stretched out and
  stacked on top of each other increases the
  polymers strength.
• (A plastic milk jug is a high-density polymer)

35
Organic Chemistry

• Cross-Linked Polymer
• Carbon branched chains that have been linked
  together by aligning them perpendicular to each
  other or by adding a substance to bind the
  carbons.
• (A pop bottle cap is a cross-linked polymer)

36
Addition Polymers

• Polymers formed by linking monomers.
• Example Formation of Polyethylene.

monomer
polymer
)x
x
(
?
ethylene
Polyethylene
37
Addition Polymers

• Polymers formed by linking monomers.
• Example Formation of PVC.

monomer
polymer
)x
x
(
?
Vinyl Chloride
PolyVinylChloride
38
Addition Polymers

• Polymers formed by linking monomers.
• Example Formation of Polystyrene, Styrofoam.

monomer
polymer
x
(
)x
?
styrene
Polystyrene
Styrofoam
39
Condensation Polymers

• Polymers formed by linking monomers and losing
  simple molecules like water (or acid) in the
  process.
• Example Production of Nylon.

1,6 - Hexanediamine
Sebacoyl Chloride
and
H
Cl
-C-C-C-C-C-C-C-C-C-C-
Cl
Cl
-C-C-C-C-C-C-
- N
N -
H
H
H
)x
Acid
(

Nylon (a polyamide)
Amide group
40
Protein chains Biological polymers

• Amino Acid
• A small molecule that is the starting molecule
  for the formation of protein chains.
• Basic amino acid contain the amine group and the
  carboxylic acid group.

H
N
H
C
H
H
Glycine is the simplest amino acid.
41
Fatty acids

• Fatty Acids
• Long hydrocarbon chains that end with the acid
  group.

H
H
H
H
H
H
H
H
H
H
H
C
H
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
CH3(CH2)10COOH
Lauric acid is a fatty acid (see pg.789 for more)
42
Fatty acids
IUPAC Name Common name
CH3CH2COOH
Propanoic acid Proprionic acid 1st fatty
acid (see pg.789)
CH3(CH2)2COOH
Butanoic acid Butyric acid Stinky feet smell
CH3(CH2)4COOH
Hexanoic acid Caproic acid
CH3(CH2)8COOH
Decanoic acid Capric acid
CH3(CH2)10COOH
Dodecanoic acid Lauric acid
CH3(CH2)14COOH
Hexadecanoic acid Palmitic acid
CH3(CH2)16COOH
Octadecanoic acid Stearic acid Inexpensive
candles made from beef fat.
43
Typical Fat

• Triglycerides
• When fatty acids are combined with glycerol.

Water is made
H
(CH2)16CH3
C
H
O
H
(CH2)16CH3
C
H
O
H
(CH2)16CH3
C
H
O
H
H
Fatty acids Stearic acid
Glycerol
44
Trigylceride Typical Fat