Intro to Organic Reactions

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Intro to Organic Reactions
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Reactions of Alkanes

• They burn!
• Hydrocarbon and Oxygen yields Carbon Dioxide and
  Water

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Reactions of Alkanes
Substitution Rxn
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Reactions of AlkenesAddition Reactions

• Alkenes are unsaturated more single bonds can
  form to the C atoms
• Molecules such as Br2, H2, HCl, HBr, and H2O add
  to the double bond

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Addition Rxn
Halogenation
C C
X2 - C - C -
X X
X Cl2, Br2, I2
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An Addition Reaction
Fat placed in Br2 vapor

• Unsaturated Fats

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An Addition Reaction

• The fat in bacon is partially unsaturated. The
  fat adds Br2 to the CC bonds.

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Addition Rxn
C C
H2 - C - C -
H H
Pt cat
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An Addition Reaction

• Fats can be hydrogenated with H2.

Saturated Fats
Peanut butter has partially hydrogenated
vegetable oil.
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Addition Rxn
C C
HX - C - C -
H
X
H
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Addition Rxn
C C
HOH - C - C -
H
OH
H
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Reactions of Aromatics

• Substitutions not additions are typical.

AlCl3 is a catalyst. Catalysts typically used in
aromatic substitutions.
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Alcohol ReactionsScreen 11.6
Eliminationthe reverse of addition
Substitution
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TYPES OF ALCOHOLS
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More Alcohol Reactions
Ethanol is a PRIMARY ALCOHOL. It is oxidized to
an ALDEHYDE and then to an ACID.
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More Alcohol Reactions
SECONDARY ALCOHOLS are oxidized to KETONES and
reaction stops there.
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Reduction of the Carbonyl Group
aldehyde ? primary alcohol
ketone ? secondary alcohol
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Acid-Base Reaction
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Acids Alcohols ? ESTERS
Condensation Reaction
Esters have generally pleasant odors
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Acids Alcohols ? ESTERS
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Aspirin, acetylsalicylic acid, Acid and Ester
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Acids Amines ? AMIDES
Condensation Reaction
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Acids Amines ? AMIDES
N-methylacetamide
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Acids Amines ? AMIDES
Acetoaminophen Tylenol, Datril, Momentum, ...
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Amino Acid Amino Acid ? Peptide
Alanine
Serine
Peptide Bond
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Polymers

• Giant molecules made by joining many small
  molecules called monomers
• Average production is 150 kg per person annually
  in the U.S.

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Polymer Classifications

• Thermoplastics (polyethylene) soften and flow
  when heated
• Thermosetting plastics soft initially but set
  to solid when heated. Cannot be resoftened.
• Other classification plastics, fibers,
  elastomers, coatings, adhesives

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Polymer Preparation

• Addition polymers directly adding monomer units
  together
• Condensation polymers combining monomer units
  and splitting out a small water (water)

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Polyethylene Addition Polymer
Ethylene
Polyethylene
A polymer with a molar mass of 1 x 106 has about
360,000 units.
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Mechanism of Addition Polymerization
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Types of Polyethylene
Branched, low density PE, LDPE
Cross-linked PE, CLPE
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Types of Polyethylene
Table 11.12 others are PVC, acrylonitrile,
polypropylene, polymethyl methacrylate
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Polystyrene

• Polystyrene is nonpolar material and dissolves in
  organic solvents.
• PS foam is mostly air, and when it dissolves it
  collapses to a much smaller volume.

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Slime!
Slime is polyvinylalcohol cross-linked with boric
acid
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Bubble Gum!A copolymer
Styrene butadiene
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Condensation Polymers
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Polyesters, PET
Jackets made from recycled PET soda bottles
Soda bottles, mylar film.
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Polyesters Mechanism
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Polymer Recycling Symbols
LDPE Low density PE 0.910-0.925 g/cm3 HDPE
High density PE 0.941-0.965 PP
Polypropylene 0.90 V PVC (Vinyl chloride)
1.30-1.58
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a POLYAMIDE
O
O

C
C
R
H
R OH
H-N N-H
OH
H
O
O
H
H
- C - R - C - N - R - N -
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Polyamides Nylon

• Each monomer has 6 C atoms in its chain.
• A polyamide link forms on elmination of HCl
• Result nylon 66

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Proteins are Polyamides
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Fats and Oils Saponification