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Intro to Organic Reactions

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 atoms

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Intro to Organic Reactions

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  1. Intro to Organic Reactions

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

  3. Reactions of Alkanes Substitution Rxn

  4. 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

  5. Addition Rxn Halogenation | | | | C = C + X2 - C - C - | | | | X X X = Cl2, Br2, I2

  6. An Addition Reaction Fat placed in Br2 vapor Unsaturated Fats

  7. An Addition Reaction The fat in bacon is partially unsaturated. The fat adds Br2 to the C=C bonds.

  8. Addition Rxn | | | | C = C + H2 - C - C - | | | | H H Pt cat

  9. An Addition Reaction • Fats can be “hydrogenated” with H2. Saturated Fats Peanut butter has partially hydrogenated vegetable oil.

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

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

  12. C H 3 A l C l 3 + H C l + C H C l 3 Reactions of Aromatics • Substitutions — not additions — are typical. AlCl3 is a catalyst. Catalysts typically used in aromatic substitutions.

  13. Alcohol ReactionsScreen 11.6 Elimination—the reverse of addition Substitution

  14. TYPES OF ALCOHOLS

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

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

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

  18. Acid-Base Reaction

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

  20. O O + H C H C O H + C H C H O H C H C O C H C H + H O 3 3 2 3 2 3 2 E t h y l a c e t a t e A c e t i c a c i d E t h a n o l Acids + Alcohols  ESTERS

  21. Aspirin, acetylsalicylic acid, Acid and Ester

  22. Acids + Amines  AMIDES Condensation Reaction

  23. Acids + Amines  AMIDES N-methylacetamide

  24. Acids + Amines  AMIDES Acetoaminophen Tylenol, Datril, Momentum, ...

  25. Amino Acid + Amino Acid  Peptide Alanine Serine Peptide Bond

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

  27. 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

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

  29. Polyethylene: Addition Polymer Ethylene Polyethylene A polymer with a molar mass of 1 x 106 has about 360,000 units.

  30. Mechanism of Addition Polymerization

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

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

  33. 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.

  34. Slime! Slime is polyvinylalcohol cross-linked with boric acid

  35. Bubble Gum!A copolymer Styrene + butadiene

  36. Condensation Polymers

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

  38. Polyesters: Mechanism

  39. 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

  40. a POLYAMIDE O O + C C R’ H R OH OH H-N N-H H O O H H - C - R - C - N - R’ - N -

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

  42. Proteins are Polyamides

  43. Fats and Oils: Saponification

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