1. Hydrocarbon Derivatives: Halocarbons Alcohols Ethers

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 –molecules not symmetrical hydrogen bonding: strongest –molecules contain H bonded to F, O, or N

5. Functional Groups 1.halocarbons 2.alcohols 3.ether 4.aldehydes 5.ketones 6.carboxylic acid 7.ester 8.amines 9.amide 10.amino acid see Table R

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

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

9. 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

10. CH 3 Cl CH 3 CHFCH 3 H H–C–Cl H chloromethane H H H H–C–C–C–H H F H 2-fluoropropane C3H7FC3H7F      

11. Naming Halides CH 3 CCl 2 CHClCH 3 C 4 H 7 Cl 3 Cl H Cl H H C – C – C – C H – C – C – C – C – H Cl Cl H trichlorobutane 2,2,3-trichlorobutane

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

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

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

15. Properties of Halocarbons alkane & alkyl halide of similar size & shape: – alkyl halide has higher bp & higher density Why? CH 4 : hydrocarbon (non-polar) bp = -162  C density = 0.423 g/ml CH 3 Cl: halogen (polar) bp = -24  C density = 0.911 g/ml stronger IMF

16. 1.516155CH 3 CH 2 CH 2 CH 2 CH 2 I 1-iodopentane 1.218130CH 3 CH 2 CH 2 CH 2 CH 2 Br 1-bromopentane 0.882108CH 3 CH 2 CH 2 CH 2 CH 2 Cl 1-chloropentane 0.79163CH 3 CH 2 CH 2 CH 2 CH 2 F 1-fluoropentane 0.62636CH 3 CH 2 CH 2 CH 2 CH 3 pentane Density (g/ml) Boiling Point (  C) Inc

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

18. Halogen Derivatives CH 3 Cl: local anesthetic (chloromethane) CHCl 3 : solvent, general anesthetic (trichloromethane) CHI 3 : antiseptic (tri-iodomethane) CCl 4 : dry cleaning solvent (tetrachloromethane) CF 2 Cl 2 : refrigerant (dichloro,difluoromethane) fluorocarbons: teflon, lubricants, synthetic blood chlorofluorocarbons: aerosol propellants, refrigerants

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

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

23. non- 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

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

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

26. more than 1 hydroxyl group use prefixes di-, tri-, tetra- –put before -ol ending –tell # of hydroxyl groups

27. Classifying Alcohols 1.by # of hydroxyl groups 2.by position of each hydroxyl group on main carbon chain

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

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

30. 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 H O H H 2-butanol (secondary)

31. H H-C-H H H H-C-C-C-H H O H H 2-methyl 2-propanol (tertiary)

32. 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

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

34. O R H O R H -- ++++ ++ -- H-bond

35. Which compound has the highest boiling point? A.CH 4 B.C 2 H 6 C.C 3 H 8 D.C 3 H 7 OH Correct response = D

38. 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

39. Properties of Ethers purepure ether: no hydrogen bonding –weak dipole-dipole interactions since polar –bent, like H 2 O ethyl ether once used as anesthesia

40. 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)

41. 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

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

43. H H H H H  C  O  C  C  C  H H H H H methylpropyl ether