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Chemistry 30 – Organic Chemistry - Part 2

Chemistry 30 – Organic Chemistry - Part 2. To accompany Inquiry into Chemistry. Organic Chemistry – 15.1 – Types of Organic Reactions. A Combustion Reactions We will focus on complete combustions: hydrocarbon + O 2 (g) CO 2 (g) + H 2 O(g) + energy

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Chemistry 30 – Organic Chemistry - Part 2

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  1. Chemistry 30 – Organic Chemistry - Part 2 To accompany Inquiry into Chemistry

  2. Organic Chemistry – 15.1 – Types of Organic Reactions • A Combustion Reactions • We will focus on complete combustions: hydrocarbon + O2(g) CO2(g) + H2O(g) + energy • Cellular respiration is a complete combustion (but H2O(l) is produced) • Many hydrocarbon derivatives also undergo complete combustion

  3. Organic Chemistry – 15.1 – Types of Organic Reactions • Do questions 1a, 2, and 3, page 589

  4. Y Z - C – C - + Y – Z C = C • Addition can occur with alkene or alkyne: • + water (HOH) alcohol • + hydrogen (H2) alkane • + hydrogen halide (HX) alkyl halide • + halogen (X2) alkyl halide seepage590-1 Organic Chemistry – 15.1 – Types of Organic Reactions • B Addition Reactions Product has more bonds! Addition

  5. A fat molecule: cis linkage O = R′ CH2 – O – C - R H H C = C C = C O = CH – O – C – R H trans linkage H R′ O = CH2 – O – C - R Organic Chemistry – 15.1 – Types of Organic Reactions • Your text has numerous examples of addition reactions on page 590 and 591 • Read about trans fats on page 592 fats are triesters!

  6. Z Y - C – C - C = C Organic Chemistry – 15.1 – Types of Organic Reactions • C Elimination Reactions • Essentially the reverse of addition – less bonds • Alcohols undergo elimination to produce water and an alkene • Alkyl halides can undergo elimination to produce alkene and hydrogen halide + Y – Z Examples on page 593

  7. - C – Y + A – Z - C – Z + A - Y Organic Chemistry – 15.1 – Types of Organic Reactions • D Substitution Reactions • Like name implies, something leaves and is replaced by something else • Examples pages 593 and 594 • Note that for halogens + alkanes, reaction is very slow (essentially doesn’t occur) without presence of ultraviolet light

  8. Organic Chemistry – 15.1 – Types of Organic Reactions • Aromatics + halogens will undergo substitution, not addition

  9. O O = = R - C – OH R - C – O - R′ Organic Chemistry – 15.1 – Types of Organic Reactions • E Esterification • Esterification is a type of elimination reaction – water is produced H2SO4 catalyst + HO - R′ + HOH carboxylicacid water alcohol ester

  10. Organic Chemistry – 15.1 – Types of Organic Reactions • Example: O H2SO4 = CH3 – CH2 – C – O - H + H - O-CH3

  11. O O H2SO4 = = CH3 – CH2 – C – O - H + H - O-CH3 CH3 – CH2 – C – O – CH3 + HOH O O = = H2SO4 CH3 – O – H + H – O – C – CH2 – CH3CH3 – O – C – CH2 – CH3 + HOH now ester is written in order of name Organic Chemistry – 15.1 – Types of Organic Reactions • Example: methyl propanoate • I prefer to write it in reverse direction (alcohol 1st) to make naming ester easier methyl propanoate

  12. Organic Chemistry – 15.1 – Types of Organic Reactions • Further esterfication examples on page 595 – 6 • Other examples page 596 • Do Practice Problems 1 – 3, page 596 – 7 • Do WS 15.1.5 • Do Investigation 15.A, page 597

  13. Organic Chemistry – 15.1 – Types of Organic Reactions • Summary:

  14. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Bromine test for double bonds • Bromine, Br2, forms a brown solution (remember electrolysis of KBr(aq) • If Br2(aq) is mixed with an alkene or alkyne, addition will occur and the brown colour will disappear in the aqueous layer • If Br2(aq) is mixed with an alkane or aromatic, substitution (slow) will occur and the aqueous layer will remain brown…………..

  15. Organic Chemistry – 15.1 – Types of Organic Reactions • Read “Octane-Enhancing Compounds” page 599 and • “Replacing CFC’s” page 600 • Section 15.1 – oral review – question 1 - reaction type

  16. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Polymer: a large long chain molecule with repeating units of small molecules called monomers • Plastics: polymers that can be heated and shaped into specific shapes and forms • Plastics are always synthetic, though not all polymers are synthetic

  17. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Addition polymerization the reaction is an addition reaction as studied earlier • Example: polyethylene CH2=CH2 + CH2=CH2-CH2-CH2-CH2-CH2- + CH2=CH2 - CH2 – CH2 –CH2 – CH2 –CH2 – CH2 –and on and on

  18. 2 2 2 Cl 2 2 Cl Cl 2 Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Other addition polymers:

  19. ester linkage Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Condensation polymerization – water produced • polyesters and nylons • polyester example:

  20. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • nylon example: amide linkage: same type of bond present between amino acids in proteins

  21. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Do Practice Problems page 606, questions 7-10

  22. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Ethene (ethylene) is required for the manufacture of many substances in Alberta’s petrochemical industry • Ethane, obtained from petroleum refining is “cracked” to produce ethene by catalytic cracking: C2H6(g) CH2=CH2(g) + H2(g) ethane ethene • Ethene is used to produce ethylene glycol (ethane-1,2-diol), polyethylene, and polyvinyl chloride Pt

  23. Cl Cl C = C (g) + Cl2(g) - C – C - (g) Cl Cl Cl - C – C – (g) C = C (g) + HCl(g) HCl from step 2 reacted with more ethene to produce more Cl Cl - C – C - Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Manufacture of PVC (polyvinyl chloride):Step 1: • Step 2: reaction type? reaction type?

  24. Cl Cl Cl Cl ………. - C – C – C – C – C – C - ………. n C = C polyvinyl chloride Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Step 3:

  25. Cl C = C Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Heath and Environmental Concerns: • Vinyl chloride: was found in the 1970’s to be carcinogenic. Workers protected today by government legislation • Manufacture and disposal of PVC may produce dioxins – highly toxic Biggest source: people burning their own garbage

  26. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Plastics do not decay or rot – problems? • Today: recycling programs – manufacture of useful products from recycled plastics • Note: recycling is not the cure-all. Reducing and reusing are better solutions. Why?

  27. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Natural Polymers • Carbohydrates: (monomer-glucose) cellulose, starch, glycogen • Proteins: (monomer-amino acids) • DNA

  28. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry • Section 15.2 Review, page 614, question 1-6

  29. Organic Chemistry – 15.2 – Polymers and the Petrochemical Industry

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