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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 alkane: 1+ H atoms replaced with halogen atoms (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. stronger IMF Properties of Halocarbons • alkane vs alkyl halide with same # C’s: • 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

  9. Naming Halides • figure out backbone name • prefixes specify halogen: fluoro, chloro, bromo, iodo • state # C attached to in backbone • gives location(s) of halogen(s) • di, tri, tetra if more than one same halogen 0

  10. hierarchy for #ing chain # chain so following on lowest C • functional group (halogens in alpha order) • multiple bonds • branches (in alpha order)

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

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

  13. 2-chloro-4-fluoro-3-iodobutane Different Halogens 4 3 2 1 chlorine 1st alphabetically: determines numbering

  14. 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:

  15. Uses of Alkyl Halides • cleaners, solvents, plastics • examples: • fluorocarbons: teflon, lubricants, synthetic blood • chlorofluorocarbons: aerosol propellants, refrigerants

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

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

  18. 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

  19. Properties of Alcohols • contain: H bonded to O atom • hydrogen bonding • alcohols: higher bp than alkane with same # C’s • ‘like dissolves like’ • alcohols tend to be very soluble in water

  20. Naming AlcohOLs • name parent chain • drop -e from -ane & replace with –ol • if 3+ carbons: state # C in chain OH group(s) attached to • more than 1 OH group: use prefixes di-, tri-, tetra- • put before -ol ending Note: never more than one OH group per C

  21. H H H H HC  CCCH OHH H H Naming H H H H HCC CCH HOHH H 1-butanol bp = 100C 2-butanol Bp = 115C

  22. Classifying Alcohols • by # of hydroxyl groups • monohydroxy alcohol: 1hydroxyl group • dihydroxy alcohol: 2OH groups • trihydroxy alcohol: 3OH groups

  23. 2. by position of hydroxyl group on C chain • 1° alcohol: -OH attached to end C of chain • 2° alcohol: -OH attached to C bonded to 2 other C’s • 3° alcohol: -OH attached to C bonded to 3 other C’s at branch point

  24. 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)

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

  26. R - O R - H O + H + H-bond

  27. R - O R - H O + H + H-bond

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

  29. Ethers • general formula ROR • where R may or may not be same as R • R and Rare hydrocarbon branches • may or may not have same # C’s • O is oxygen bridge

  30. Properties of Ethers • pure ether: no hydrogen bonding • weak dipole-dipole interactions since polar • ethers are not linear • they are bent, like H2O • ethyl ether once used as anesthesia

  31. Properties of Ethers same # C’s: alcohol ether alkane • 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)

  32. 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

  33. methyl ether (make correction to 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

  34. methylpropyl ether H H H H HCOCCCH H H H H

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