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Hydrocarbon Derivatives:

Halocarbons Alcohols Ethers. Hydrocarbon Derivatives:. Hydrocarbons. c ontain only carbon & hydrogen carbon can also form strong covalent bonds with other elements such as: O, N, F, Cl, Br, I, S, & P. Functional Group. functional group :

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Hydrocarbon Derivatives:

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  1. Halocarbons Alcohols Ethers Hydrocarbon Derivatives:

  2. Hydrocarbons • contain only carbon & hydrogen • carbon can also form strong covalent bonds with other elements such as: O, N, F, Cl, Br, I, S, & P

  3. Functional Group • functional group: atom or group atoms in organic molecule that always behaves the same way • adding functional group changes chemical & physical properties of molecule in specific ways • changes depend on type functional group added

  4. Intermolecular Forces • determine boiling point & solubility • van der Waals (dispersion):weakest • nonpolar molecules • dipole-dipole:intermediate strength • molecule has atoms with different electronegativities • molecules not symmetrical • hydrogen bonding:strongest • molecules contain H bonded to F, O, or N

  5. see Table R Functional Groups • halocarbons • alcohols • ether • aldehydes • ketones • carboxylic acid • ester • amines • amide • amino acid

  6. Halocarbons/Halogens/Organic Halides • one (or more) hydrogen atoms in alkane is replaced with halogen atom (F, Cl, Br, or I) • no longer hydrocarbons! • called halocarbons, alkyl halides or organic halides

  7. Table R • general formula halocarbons: R-X • R represents entire hydrocarbon part of molecule • X represents halogen (F, Cl, Br, or I)

  8. Naming Halides • figure out backbone name • prefixes specify halogen: fluoro, chloro, bromo, iodo • di, tri, tetra if more than one same halogen • state # C attached to in backbone • gives location(s) of halogen(s) 0 Note: follow same basic rules learned so far • # chain so halogen has lowest # • halogen # takes precedent over multiple bonds and branches

  9.        C3H7F CH3Cl CH3CHFCH3 H H H H–C–C–C–H HFH H H–C–Cl H 2-fluoropropane chloromethane

  10. Naming Halides CH3CCl2CHClCH3 C4H7Cl3 HCl H H H –C – C – C – C– H HCl Cl H 2,2,3-trichlorobutane

  11. Ranking Halogens • if more than 1 kind halogen atom present – name them alphabetically • lowest # goes to halogen alphabetically first

  12. 2-chloro-4-fluoro-3-iodobutane Different Halogens 4 3 2 1 chlorine 1st alphabetically: determines numbering

  13. Br CH3CH2CHCHCH3 I 3-bromo 2-iodo pentane F Cl HCCH F Cl 1,1-dichloro-2,2-difluoroethane Name:

  14. stronger IMF Properties of Halocarbons • alkane & alkyl halide of similar size & shape: • alkyl halide has higher bp & higher density Why? • CH4: hydrocarbon (non-polar) bp = -162C density = 0.423 g/ml • CH3Cl: halogen (polar) bp = -24C density = 0.911 g/ml

  15. Boiling Point (C) Density (g/ml) CH3CH2CH2CH2CH3 pentane 36 0.626 CH3CH2CH2CH2CH2F 1-fluoropentane 63 0.791 Inc Inc CH3CH2CH2CH2CH2Cl 1-chloropentane 108 0.882 CH3CH2CH2CH2CH2Br 1-bromopentane 130 1.218 CH3CH2CH2CH2CH2I 1-iodopentane 155 1.516

  16. Uses of Alkyl Halides • cleaners, solvents, plastics • examples: • Teflon & PVC’s • refrigerants (used to be chlorofluorocarbons- now hydrofluorocarbons)

  17. Halogen Derivatives • CH3Cl: local anesthetic (chloromethane) • CHCl3: solvent, general anesthetic (trichloromethane) • CHI3: antiseptic (tri-iodomethane) • CCl4: dry cleaning solvent (tetrachloromethane) • CF2Cl2: refrigerant (dichloro,difluoromethane) • fluorocarbons: teflon, lubricants, synthetic blood • chlorofluorocarbons: aerosol propellants, refrigerants

  18. OH H HCOH H H HCH H     Alcohols • OH group replaces H in hydrocarbon • OH group called hydroxyl group

  19. Table R • general formula Alcohols: ROH • R represents entire hydrocarbon part of molecule • OH is hydroxyl group

  20. alcohols are non-electrolytes! • hydroxyl group (hydroxide ion of bases) - does not form ions in water! (no metal like bases) • hydroxyl group is polar • alcohols soluble in water

  21. Naming AlcohOLs • based on alkane name • name parent chain • drop –e ending & replace with –ol • # C OH group(s) attached to (if 3+ carbons)

  22. H H H H HCCCCH OHH H H Note: never more than one OH group per C Naming H H H H HCCCCH HOHH H 1-butanol bp = 100C 2-butanol Bp = 115C

  23. more than 1 hydroxyl group • use prefixes di-, tri-, tetra- • put before -olending • tell # of hydroxyl groups

  24. Classifying Alcohols • by # of hydroxyl groups • by position of each hydroxyl group on main carbon chain

  25. # hydroxyl groups • monohydroxy alcohol: 1 hydroxyl group • dihydroxy alcohol: 2 OH groups • trihydroxy alcohol: 3 OH groups

  26. position of hydroxyl group: monohydroxy alcohols • primary alcohol: -OH group attached to end C of chain • secondary alcohol: -OH group attached to C bonded to 2 other C’s • tertiary alcohol: -OH group attached to C at branch point (C bonded to 3 other C’s)

  27. H H H H H-C-C-C-C-O-H H H H H 1-butanol (primary) H H H H H-C-C-C-C-H H HO H H 2-butanol (secondary)

  28. H H-C-H H H H-C-C-C-H HOH H 2-methyl 2-propanol (tertiary)

  29. H H H-C─C-H O O H H H H H H-C─C─C-H O O O H H H dihydroxy trihydroxy

  30. Properties of Alcohols • contain: H bonded to O atom • hydrogen bonding • alcohols: higher bp than corresponding alkane • ‘like dissolves like’ • alcohols tend to be very soluble in water

  31. R - O R - H O + H + H-bond

  32. Correct response = D Which compound has the highest boiling point? • CH4 • C2H6 • C3H8 • C3H7OH

  33. Ethers • general formula ROR • where R may or may not be same as R • R and Rare hydrocarbon branches • O is oxygen bridge • ethers are not linear • they are bent, like water

  34. Properties of Ethers • pure ether: no hydrogen bonding • weak dipole-dipole interactions since polar • bent, like H2O • ethyl ether once used as anesthesia

  35. Properties of Ethers • compared to alkanes with same # C’s: • higher bp’s than alkanes (ethers have greater mass due to O) • more soluble in water than alkanes (ethers are polar, alkanes are not) • compared to alcohols with same # C’s: • lower bp’s than similar alcohols (ethers don’t have H-bonds, alcohols do) • much less soluble in water than alcohols (ethers less polar than alcohols)

  36. Naming Ethers • if both hydrocarbon branches identical: • name branch only once followed by ether • if 2 branches are different: • list names alphabetically followed by ether

  37. methyl ether (correct on Table R) propyl ether H H HCOCH H H H H H H H H HCCCOCCCH H H H H H H

  38. methylpropyl ether H H H H HCOCCCH H H H H

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