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ORGANIC CHEMISTRY

ORGANIC CHEMISTRY. 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. General Characteristics of Organic Compounds. Nonpolar

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ORGANIC CHEMISTRY

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  1. ORGANIC CHEMISTRY

  2. 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

  3. 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

  4. 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:

  5. Bonding • Carbon- has 4 valence electrons, needs 4 more, forms4 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

  6. Homologous Series (Families) • Group of related compound in which each member has one more group • Ex: CH3CH2CH3 and CH3CH2CH2CH3 • 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

  7. Hydrocarbons • Organic compounds that contain only CARBON and HYDROGEN ALKANES... SINGLE bonds between Carbons Saturated hydrocarbon CnH2n+2 Family Name ALKENES... ONE DOUBLE bond between two Carbons Unsaturated hydrocarbon CnH2n ALKYNES... ONE TRIPLE bond between two Carbons Unsaturated Hydrocarbon CnH2n-2

  8. PREFIXES …counting the CARBONS

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

  10. 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 1st carbon Example: 2-Pentene

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

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

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

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

  15. Naming Branched Hydrocarbons • Find the longest continuous chain, name it • To name the branches: number of carbons + “-yl” • Examples: • CH3 = methyl • CH2CH3 = 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

  16. isomers SAME…BUT DIFFERENT • Same – number and type of atoms • Different – structure and name • Have different physical and chemical properties 2 CARBONS 6 HYDROGENS 1 OXYGEN ETHANOL a primary alcohol DIMETHYL ETHER CH3OCH3 C2H5 OH

  17. GROUPS and COMPOUNDS

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

  19. 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: • Methanol • 2-Propanol

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

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

  22. 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

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

  24. diols dihydroxy alcohols 2 -OH groups are present Example: 1,2 ethanediol

  25. triols trihydroxy alcohols 3 -OH groups are present Example: 1,2,3 propanetriol

  26. ACIDS • 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

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

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

  29. ETHER • 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

  30. ESTER • 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

  31. Ester Examples • Ethyl Methanoate • Ethyl Ethanoate

  32. AMINES • Functional Group: NH2 • Name the chain, add “amine” to the end ethanamine C2H5NH2

  33. AMIDES • Functional Group: R-CONH2 • Name: Name the chain, add “amide” to the end Butanamide Propanamide

  34. AMINO ACIDS • Functional Groups: -NH2 and –COOH

  35. Thiols • Just like an alcohol, but –SH instead of –OH Example: Methyl Thiol (CH3SH)

  36. SUBSTITUTION ADDITION ESTERIFICATION SAPONIFICATION POLYMERIZATION COMBUSTION FERMENTATION REACTIONS

  37. Substitution • Something takes the place of something else • Starts with a saturated hydrocarbon • 2 reactants, 2 products Ethane Chlorine

  38. Addition • Start with an unsaturated hydrocarbon • Break the double (or triple) bond • Add in an atom (or group) • 2 reactants, 1 product Ehtene Cl2 1,2 Dichloroethane

  39. ESTERIFICATION Concentrated H2SO4 acts as a dehydrating agent ORGANIC ACID + ALCOHOL H2SO4 ESTER + WATER Propanoic Acid Methanol Methyl Propanoate H2O

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

  41. Fermentation C6H12 O6 enzyme C2H5 OH CO2 CARBON DIOXIDE GLUCOSE ETHANOL

  42. COMBUSTION • Hydrocarbon + O2 CO2 + H2O • Exothermic Example: C2H6 + O2

  43. Poly...poly...poly…poly...poly...polymerization polymerization • Chains of small units make up a MACROMOLECULE • Examples: Plastics, proteins

  44. 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

  45. Addition Polymerization • Bonding of monomers of unsaturated compounds by “opening” a multiple bond in the carbon chain • Example: polyethylene and many plastics nC2H4 (C2H4)n

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