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Homologous series (reminder) Cis -trans Isomer (reminder)

Homologous series (reminder) Cis -trans Isomer (reminder). Warm-up. What is a possible struc form for a molecule with… Ketone C 4 H 8 O Aldehyde C 6 H 12 O Carboxylic acid C 5 H 10 O 2 Halide C 2 H 5 Cl. Warm-up II. What is more soluble in water, propanone , or 2 – propanol ? Why?

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Homologous series (reminder) Cis -trans Isomer (reminder)

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  1. Homologous series (reminder) • Cis-trans Isomer (reminder)

  2. Warm-up • What is a possible struc form for a molecule with… • Ketone C4H8O • Aldehyde C6H12O • Carboxylic acid C5H10O2 • Halide C2H5Cl

  3. Warm-up II • What is more soluble in water, propanone, or 2 – propanol? Why? • What is the structural formula for 2, 2–dimethylbutane? • Write the reaction for the chlorination of ethane.

  4. Warm-up III • Naming/formula issues • Determine longest chain • Order of priority • Functional groups determine the end of the name • Except halides (they are not a priority) • Alphabetic order for alkyl groups

  5. Reactions of Alkanes • Combustion • Complete and Incomplete • Halogenation • Mech. (I, P, T) & a connection to O3 • Why not more? • Alkanes are not very reactive due to the strength of the C – C bond and the lack of polarization • Let’s start a reactions map. • So far we have Alkane haloalkane

  6. Ozone • How does ozone work?

  7. Alkenes • Much more reactive • What is a DB? • Why might it be more reactive?

  8. Alkenes • Addition reactions • Let’s start w/ simplest alkene • What happens when we add • H2 • Br2 • HBr • H2O (with H2SO4 catalyst) • Add these to the map

  9. Alkenes • Uses of Alkene reactions • Bromination: Used to detect presence of alkenes. Color change. • Hydration: Much of the EtOH produced comes from this process. Ethene is produced in refining of petroleum. • Hydrogenation: Margarine etc.

  10. Reactions So Far

  11. Polymerization of Alkenes • Polymers are long chains of repeating units • Like a train • Linking units of ethene produce polyethene (polythene) (#2 HDPE or #4 LDPE) • Phenylethene produces poly-phenylethene (#6 PS) • If you start with chloroethene you get polychloroethene (AKA polyvinylchloride) (#3 V) • If you start with tetrafluoroethene you get poly tetrafluoroethene (PTFE) or Teflon

  12. Alcohols • Now that we know how to produce alcohols non-biologically, what can we do with it? • Combustion • Importance? • Oxidation using acidified-dichromate solution • 1st product: ethanal (what is this?) and water • 2nd product: Ethanoic acid (what is this?) • Could this same process make a Ketone? • What type of carbon would be needed?

  13. Reactions So Far

  14. Reactions of Haloalkanes • Substitution reactions: Meaning that the halogen goes away • Example: OH- subs a Chlorine in chloromethane • What do you get? • How does it happen? (mechanism)

  15. Nucleophilic Substitution • Nucleophile – substance with electrons available for bonding (L.P.) therefore attracted to a nucleus • Polarity of C-halo bond • Two types of mechanisms: • SN2 (single step, primary haloalkanes) • Rate = k [X] [A] • Bimolecular (that’s why SN2) • SN1 (multi-step, tertiary haloalkanes) • Rate = k [X] • Unimolecular

  16. Reactions So Far Trihaloalkanes Tetrahaloalkanes M M

  17. Practice • Write a reaction for each of the following: • Make an alcohol from Propene • Make a Ketone out of 2-butanol • Chloroethane from ethane • Dichloroethane from chloroethane • Pentanoic acid from pentanol • Challenge: Methyl ethanoate(Hint: what functional group is this?)

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