Organic Reactions

1
Organic Reactions
2
Combustion

• Reaction with O2 burning
• For hydrocarbons, products of complete combustion
  are CO2 H2O
• Insufficient O2 C, CO, H2O
• C3H8(g) 5O2(g) ? 3CO2(g) 4H2O(g)

3
Substitution

• Start with a saturated hydrocarbon
• Replace 1 or more H atom with another atom
  or group. Get 2 products (swap).

• C2H6 Cl2 ? C2H5Cl HCl
• H?C?C?H Cl?Cl ? H?C?C?H HCl

H H
H Cl
H H
H H
4
Addition

• Add across a double or triple bond.
• Start with an unsaturated hydrocarbon.
• Get only 1 saturated product. (1 answer)

• H?CC?H Cl?Cl ? H?C?C?H

C2H4 Cl2 ? C2H4Cl2
H H
Cl Cl
H H
5
Esterification

• Organic Acid Alcohol ? Ester Water
• H?C?C?OH HO?C?C?C?H ?

O
H H H
H

H H H
H
O
H ?
H H H

H?C?C?O?C?C?C?H H2O
? H
H H H
6
Saponification

• Making Soap
• Fat Base ? Glycerol Soap

7
H ? C ? C ? C ? H
O

H?
?O?C?C17H35
NaOH NaOH NaOH
O

?O?C?C17H35
H?
?

O

?O?C?C17H35
H?
FAT Base ?
(Triglyceride)
8
H ? C?OH ? C?OH ? C?OH ? H
O

Na?O?C?C17H35
H?
O


H?
Na?O?C?C17H35
O
H?

Na?O?C?C17H35
Soap
Glycerol
9
Fermentation

• Sugars are broken down into alcohol CO2
• C6H12O6 ? 2C2H5OH 2CO2

zymase
carbon dioxide
sugar
ethanol
10
What do the protein in eggs, the plastic in pop
bottles, and the nylon in stockings have in
common?

• They are all giant molecules called polymers.
• Poly means many
• Mers means parts

11
Polymers

• Very large molecules consisting of many repeating
  structural units.
• Analogy chain consisting of many links
• Masses can be gt 1,000,000 amu
• Monomer Molecule from which a polymer is made.
  Starting material.

12
Natural Polymers

• Wool
• Silk
• Rubber
• Starch
• Proteins
• Nucleic Acids

13
Synthetic Polymers

• Plastics polyethylene, PVC
• Synthetic Fibers nylon, rayon, polyester
• Rubber Substitutes polyurethane
• Polymerization reaction that produces a polymer

14
Polymerization Reactions

• Addition start with unsaturated monomers.
  Everything in reactants goes into polymer. Only
  1 product, saturated.
• Condensation monomers containing 2 functional
  groups combine with the loss of a small
  by-product, usually H2O.

15
Addition Polymerization
segmer
H
H
H H H H H H ? ? ? ? ?
? ?C?C?C?C?C?C? ? ? ? ? ? ? H H H H
H H
?
?
n
CC
?
?
?
H
H
Ethene monomer
n
Polyethylene polymer
16
Polyethylene Varieties

• Milk bottles, detergent bottles, oil bottles,
  toys, plastic grocery bags
• Shrink-wrap films, sandwich bags, garment bags,
  grocery bags
• Bottle caps

17
Substituted Ethylenes

• H H
• CC
• H CH3

H H H H H H H H ?C?C?C?C?C?C?C?C? H
? H ? H ? H ?
?
CH3
CH3
CH3
CH3
Indoor-outdoor carpet, upholstery
18
Polyvinyl Chloride (PVC)

• H H
• CC
• H Cl

H H H H H H H H ?C?C?C?C?C?C?C?C? H
Cl H Cl H Cl H Cl
?
Phonograph records, garden hoses, pipes Replace
the Hs with Cl you get Saran wrap.
19
Teflon

• F F
• CC
• F F

F F F F F F ?C?C?C?C?C?C? F F F F
F F
n
?
20
Condensation Polymerization
H H H?O?C?C?O?H H H
H H H?O?C?C?O?H H H

H H H H H?O?C?C?O?C?C?O?H
H H H H

?
H2O
21
Condensation Polymerization

• Split out a small molecule such as H2O.
• Monomer has to have a functional group at each
  end.

22
Nylon - 1935

• HO?C?C?C?C?C?C?OH

O
O



?
NH2?C?C?C?C?C?C?NH2
O
O
H
H


?
?
?C?C?C?C?C?C?N?C?C?C?C?C?C?N?
n
H2O
23
Congratulations!!!! Youre finished!
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