Topic 10 & 20 reaction summary and review

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Topic 10 & 20 reaction summary and review

  1. 1. IB Chemistry Power Points Topics 10 & 20 Organic Chemistrywww.pedagogics.ca Reaction Summary
  2. 2. Reactions and Mechanisms SL and HL
  3. 3. Conc OH-, ethanol, Δ (elimination) 1o or 2o R-X 3o R-X Homolytic fission, UV light (substitution) KCN SN1 H2, Ni catalyst, NaOH, Δ (substitution) Δ, pressureH2, Ni catalyst, Δ (addition) 3o R-X (reduction) SN2 1o R-X (addition) X2 or HX, Δ (condensation) with R-COOH (addition) H2O, [H2SO4], Δ polymerization addition (oxidation) H+,Cr2O72-, Δ reflux (condensation) with R-OH
  4. 4. SL CorePathways
  5. 5. Combustion reactions not included in this summary. You are still responsible for thestoichiometry of these reactions, problems using PV=nRT, andempirical formula – combustion analysis problems Only two mechanisms are required at SL - Homolytic fission - Nucleophilic substitution
  6. 6. Homolytic fission, UV light Alkane Reactions Making halogenoalkanes by process of homolytic fission. Know what a radical is Understand and memorize the the 3 steps – Initiation, Propagation and Termination This reaction REQUIRES light
  7. 7. Homolytic fission, UV light Alkene Addition Reactions With hydrogen gas to makeH2, Ni catalyst, Δ (addition) alkanes
  8. 8. Homolytic fission, UV light Alkene Addition Reactions With hydrogen gas to makeH2, Ni catalyst, Δ (addition) alkanes With halogens or HX’s to make halogenoalkanes (R-X) (addition) X2 or HX, Δ
  9. 9. Homolytic fission, UV light Alkene Addition Reactions With hydrogen gas to makeH2, Ni catalyst, Δ (addition) alkanes With halogens or HX’s to make halogenoalkanes (R-X) (addition) X2 or HX, Δ With water to make alcohols (R-OH) (addition) H2O, [H2SO4], Δ
  10. 10. Homolytic fission, UV light Alkene Addition Reactions With hydrogen gas to makeH2, Ni catalyst, Δ (addition) alkanes With halogens or HX’s to make halogenoalkanes (R-X) (addition) X2 or HX, Δ With water to make alcohols (R-OH) (addition) H2O, [H2SO4], Δ Monomer subunits combine to polymerization make polymers addition
  11. 11. Oxidation of Alcohols Be able to recognize 1o, 2o and 3o alcohols Oxidizing agent is usually potassium dichromate. As dichromate ions are reduced color changes from orange to green Reflux – heated mixture is2o R-OH are oxidized to (oxidation) condensed and re-reactedketones. 3o are resistant H+,Cr2O72-, Δ refluxto oxidation 1o R-OH are oxidized first to aldehydes and then to carboxylic acids
  12. 12. Nucleophilic Substitution NaOH, Δ (substitution)Be able to recognize 1o, 2o and 3ohalogenoalkanes
  13. 13. Nucleophilic Substitution SN1 NaOH, Δ (substitution) 3o R-X3o halogenoalkanes react withOH- to make alcohols by SN1mechanism. (carbocationintermediate)
  14. 14. Nucleophilic Substitution NaOH, Δ (substitution)1o halogenoalkanes react withOH- to make alcohols by SN2mechanism. (transition state) SN2 1o R-X
  15. 15. Homolytic fission, UV light SN1 NaOH, Δ (substitution)H2, Ni catalyst, Δ (addition) 3o R-X SN2 1o R-X (addition) X2 or HX, Δ (addition) H2O, [H2SO4], Δ polymerization addition (oxidation) H+,Cr2O72-, Δ reflux
  16. 16. HLPathways
  17. 17. Conc OH-, ethanol, Δ (elimination) 1o or 2o R-X 3o R-X Homolytic fission, UV light (substitution) KCN SN1 H2, Ni catalyst, NaOH, Δ (substitution) Δ, pressureH2, Ni catalyst, Δ (addition) 3o R-X (reduction) SN2 1o R-X (addition) X2 or HX, Δ (condensation) with R-COOH (addition) H2O, [H2SO4], Δ polymerization addition (oxidation) H+,Cr2O72-, Δ reflux (condensation) with R-OH
  18. 18. HL adds nucleophilic substitution reactions with cyanide ion acting as the nucleophile and (substitution) KCNSN13o R-XSN21o R-X
  19. 19. HL adds nucleophilic substitution reactions with cyanide ion acting as the nucleophile and with ammonia (substitution) KCNSN13o R-XSN21o R-X
  20. 20. Nitriles can be REDUCED to amines in different ways H2, Ni catalyst, Δ, pressure (reduction)
  21. 21. Conc OH-, ethanol, Δ (elimination) Elimination reaction mechanisms compete with substitution when halogenoalkanes react with some nucleophiles Product is an alkene Which mechanism is favored depends on the reaction conditions
  22. 22. Conc OH-, ethanol, Δ (elimination) 1o or 2o R-X3o R-X Elimination reaction mechanisms compete with substitution when halogenoalkanes react with some nucleophiles Product is an alkene Which mechanism is favored depends on the reaction conditions
  23. 23. Condensation reactions includeEsterification – where an ester andwater are formed by the reactionbetween a carboxylic acid and analcohol (condensation) with R-OH
  24. 24. Condensation reactions include– where an amide and water areformed by the reaction between acarboxylic acid and an amine (condensation) with R-COOH (condensation) with R-OH
  25. 25. Conc OH-, ethanol, Δ (elimination) 1o or 2o R-X 3o R-X Homolytic fission, UV light (substitution) KCN SN1 H2, Ni catalyst, NaOH, Δ (substitution) Δ, pressureH2, Ni catalyst, Δ (addition) 3o R-X (reduction) SN2 1o R-X (addition) X2 or HX, Δ (condensation) with R-COOH (addition) H2O, [H2SO4], Δ polymerization addition (oxidation) H+,Cr2O72-, Δ reflux (condensation) with R-OH

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