2. ORGANIC CHEMISTRY

3. Organic Chemistry Study of carbon and carbon compounds Organic compounds contain carbon atoms which covalently bond to each other in chains, rings, and networks to form a variety of structures

4. General Characteristics of Organic Compounds Nonpolar Soluble in nonpolar solvents / insoluble in polar solvents (water) “Like dissolves Like” Poor conductors of heat and electricity –Exception: aqueous organic acids conduct Low melting and boiling points React slower than inorganic compounds

5. Structural Formulas –Attempts to show the bonding patterns and approximate shapes –Ex: Condensed Structural Formulas –Shows the connections without showing the shape and bonds –Ex:

6. Bonding Carbon- has 4 valence electrons, needs 4 more, forms 4 bonds Hydrogen – has 1 valence electron, needs 1 more, forms 1 bond Oxygen – has 6 valence electrons, needs 2 more, forms 2 bonds Nitrogen – has 5 valence electrons, needs 3 more, forms 3 bonds Halogens (group 17) – has 7 valence electrons, needs 1 more, forms 1 bond

7. Homologous Series (Families) Group of related compound in which each member has one more group –Ex: CH 3 CH 2 CH 3 and CH 3 CH 2 CH 2 CH 3 Members of a group will have similar structures and properties As the members of a series increase in mass, their boiling (and melting) points increase – due to increased intermolecular forces

8. Hydrocarbons Organic compounds that contain only CARBON and HYDROGEN ALKANES... SINGLE bonds between Carbons Saturated hydrocarbon C n H 2n+2 ONE TRIPLE bond between two Carbons Unsaturated Hydrocarbon ONE DOUBLE bond between two Carbons Unsaturated hydrocarbon C n H 2n C n H 2n-2 ALKYNES... ALKENES... Family Name

10. …counting the CARBONS PREFIXES

11. ALKANES Contain all single bonds Naming: carbon prefix + -ane Examples: Octane Butane

12. ALKENES Contain 1 double bond Naming: carbon prefix + -ene –A number is used in front to indicate the location of the double bond –If a number is not indicated the double bond comes after the 1 st carbon Example: 2-Pentene

13. Diene Contains 2 double bonds Naming: location-carbon prefix-diene Example: 1,3-pentadiene

14. ALKYNES Contains 1 triple bond Naming: location - carbon prefix + -yne Examples: 3 – hexyne Propyne

15. Saturated Compounds – contains all single carbon-carbon bonds Unsaturated Compounds – contains at least one multiple carbon-carbon bond

16. Branched Hydrocarbons Contain 1 or more branches off the main chain 8 7 6 5 4 3 2 1 Methyl group on carbon 4 4-methyl-ocatane

17. Naming Branched Hydrocarbons Find the longest continuous chain, name it To name the branches: number of carbons + “-yl” –Examples: CH 3 = methyl CH 2 CH 3 = ethyl The location of the alkyl (branched group) is indicated –If there is more than one of the same branch, use prefixes (di, tri, tetra, …) –The carbon chain must be numbered from the end that will give the lowest numbers for the branches Example: 2, 2, 3 – trimethyl pentane

18. SAME…BUT DIFFERENT 2 CARBONS 6 HYDROGENS 1 OXYGEN ETHANOL a primary alcohol DIMETHYL ETHER C 2 H 5 OH CH 3 OCH 3 Same – number and type of atoms Different – structure and name  Have different physical and chemical properties

19. GROUPS and COMPOUNDS

20. Functional Group: halogen (group 17 element) Name: location-halide-carbon chain Examples: 1. 2-bromobutane 2. 1,3 - dichloropentane

21. ALCOHOLS Functional Group: -OH No more than one –OH group can be attached to any one carbon The carbon to which the –OH group is attached must have all single bonds Alcohols are not bases (do not ionize in water) Name: hydrocarbon name, replace the final –e with –ol Examples: 1.Methanol 2.2-Propanol

22. Types of Alcohols Monohydroxy – contain 1 –OH group –Primary –Secondary –Tertiary Dihydroxy (Diol) – contain 2 –OH groups Trihydroxy (Triol) – contain 3 –OH groups

23. Primary Alcohols Contain 1 –OH group -OH group is attached to the end of the chain Examples: 1.Ethanol 2.Propanol

24. H SECONDARY ALCOHOL R-C-R O H Contain 1 –OH group Carbon that is attached to the –OH group is attached to 2 other carbon atoms 2-Butanol

25. R TERTIARY ALCOHOL R-C-R O H 2METHYL,2-BUTANOL Contain 1 –OH group Carbon attached to the –OH group is attached to three other carbon atoms

26. 2 -OH groups are present Example: 1,2 ethanediol

27. 3 -OH groups are present Example: 1,2,3 propanetriol

28. Functional Group = -COOH Name: Hydrocarbon name, drop the final “e” and replace it with “–oic” followed by the word “acid” Examples: 1. Ethanoic Acid 2. Butanoic Acid

29. ethanal 2 carbons alkane aldehyde Functional Group: -CHO Name: drop the final “e” and add “-al” Propanal

30. Propanone Functional Group: -CO- Name: Hydrocarbon name, drop the final “e”, add “one” 2-Butanone

31. Functional group: -O- (chain-O-chain) Name: 1. Name each hydrocarbon chain – drop the ending add “yl” 2. Add “ether” to the end diethyl ether Ethyl methyl ether

32. Functional Group: -COOR Formed from a dehydration reaction of an alcohol and an acid Fruity odor Name: Name each hydrocarbon chain –The part with the –CO gets the “-oate” ending –The other part gets the “-yl” ending

33. Ester Examples Ethyl Methanoate Ethyl Ethanoate

34. ethanamine C 2 H 5 NH 2 Functional Group: NH 2 Name the chain, add “amine” to the end

35. Butanamide Propanamide Functional Group: R-CONH 2 Name: Name the chain, add “amide” to the end

36. Functional Groups: -NH 2 and –COOH

37. Just like an alcohol, but –SH instead of – OH Example: Methyl Thiol (CH 3 SH)

38. SUBSTITUTION ADDITION ESTERIFICATION SAPONIFICATION POLYMERIZATION COMBUSTION FERMENTATION

39. EthaneChlorine Something takes the place of something else Starts with a saturated hydrocarbon 2 reactants, 2 products

40. EhteneCl 2 1,2 Dichloroethane Start with an unsaturated hydrocarbon Break the double (or triple) bond Add in an atom (or group) 2 reactants, 1 product

41. ORGANIC ACID + ALCOHOL H 2 SO 4 ESTER + WATER Propanoic Acid Methanol Methyl Propanoate H2OH2O Concentrated H 2 SO 4 acts as a dehydrating agent

42. FAT (glycerol ester) Strong base (NaOH or KOH) SOAPglycerol (trihydroxy alcohol) 1,2,3 propane triol Reverse of esterification, carried out in the presence of a base

43. GLUCOSE enzyme ETHANOL CARBON DIOXIDE C 6 H 12 O 6 C 2 H 5 OHCO 2

44. Hydrocarbon + O 2 CO 2 + H 2 O Exothermic Example: C 2 H 6 + O 2

45. Poly...poly...poly…poly...poly...polymeri zation Chains of small units make up a MACROMOLECULE Examples: Plastics, proteins

46. Condensation Polymerization Bonding of monomers by a dehydration reaction –OH groups of adjacent alcohols react, water is removed, the 2 molecules are connected by the remaining O Examples: Nylon, Protein, Polyester

47. Addition Polymerization Bonding of monomers of unsaturated compounds by “opening” a multiple bond in the carbon chain Example: polyethylene and many plastics n C2H4n C2H4 (C 2 H 4 ) n