Intro to Organic Reactions

Reactions of Alkanes They burn! Hydrocarbon and Oxygen yields Carbon Dioxide and Water

Reactions of Alkanes Substitution Rxn

Reactions of Alkenes Addition Reactions Alkenes are unsaturated — more single bonds can form to the C atomsAlkenes are unsaturated — more single bonds can form to the C atoms Molecules such as Br 2, H 2, HCl, HBr, and H 2 O add to the double bondMolecules such as Br 2, H 2, HCl, HBr, and H 2 O add to the double bond

Addition Rxn | | | | C = C + X 2 - C - C - | | | | X X X = Cl 2, Br 2, I 2 Halogenation

An Addition Reaction Fat placed in Br 2 vapor Unsaturated Fats

An Addition Reaction The fat in bacon is partially unsaturated. The fat adds Br 2 to the C=C bonds.

Addition Rxn | | | | C = C + H 2 - C - C - | | | | H H Pt cat

An Addition Reaction Fats can be “hydrogenated” with H 2.Fats can be “hydrogenated” with H 2. Peanut butter has partially hydrogenated vegetable oil. Saturated Fats

Addition Rxn | | | | C = C + HX - C - C - | | | | H X H+H+

Addition Rxn | | | | C = C + HOH - C - C - | | | | H OH H+H+

Reactions of Aromatics SubstitutionsSubstitutions — not additions — are typical. AlCl 3 is a catalyst. Catalysts typically used in aromatic substitutions. + CH 3 Cl CH 3 + HCl AlCl 3

Alcohol Reactions Screen 11.6 Substitution Elimination—the reverse of addition

TYPES OF ALCOHOLS

More Alcohol Reactions Ethanol is a PRIMARY ALCOHOL. It is oxidized to an ALDEHYDE and then to an ACID.

More Alcohol Reactions SECONDARY ALCOHOLS are oxidized to KETONES — and reaction stops there.

Reduction of the Carbonyl Group aldehyde  primary alcohol ketone  secondary alcohol

Acid-Base Reaction

Acids + Alcohols  ESTERS Esters have generally pleasant odors Condensation Reaction

Acids + Alcohols  ESTERS H + OO CH 3 COH + CH 3 CH 2 OHCH 3 COCH 2 CH 3 + H 2 O Acetic acidEthanol Ethyl acetate

Aspirin, acetylsalicylic acid, Acid and Ester

Acids + Amines  AMIDES Condensation Reaction

Acids + Amines  AMIDES N-methylacetamide

Acetoaminophen Tylenol, Datril, Momentum,... Acetoaminophen Tylenol, Datril, Momentum,...

Amino Acid + Amino Acid  Peptide AlanineSerine Peptide Bond

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

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

Polymer Preparation Addition polymers — directly adding monomer units togetherAddition polymers — directly adding monomer units together Condensation polymers — combining monomer units and splitting out a small water (water)Condensation polymers — combining monomer units and splitting out a small water (water)

Polyethylene: Addition Polymer EthylenePolyethylene A polymer with a molar mass of 1 x 10 6 has about 360,000 units.

Mechanism of Addition Polymerization

Types of Polyethylene Linear, high density PE (HDPE) Branched, low density PE, LDPE Cross-linked PE, CLPE

Types of Polyethylene Table 11.12: others are PVC, acrylonitrile, polypropylene, polymethyl methacrylate

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

Slime! Slime is polyvinylalcohol cross-linked with boric acid

Bubble Gum! A copolymer Styrene + butadiene Styrene + butadiene

Condensation Polymers

Polyesters, PET Jackets made from recycled PET soda bottles Soda bottles, mylar film.

Polyesters: Mechanism

Polymer Recycling Symbols LDPE = Low density PE = g/cm 3 HDPE = High density PE = PP = Polypropylene = 0.90 V = PVC (Vinyl chloride) =

C R OH O R’ H-N N-H + C O OH H H - C - R - C - N - R’ - N - O O a POLYAMIDE HH

Polyamides: Nylon Each monomer has 6 C atoms in its chain.Each monomer has 6 C atoms in its chain. A polyamide link forms on elmination of HClA polyamide link forms on elmination of HCl Result = nylon 66Result = nylon 66

Proteins are Polyamides

Fats and Oils: Saponification