Unit 14- Organic Chemistry.pptxUnit 14- Organic Chemistry

Unit 14- Organic Chemistry

1. Unit 13 ORGANIC CHEMISTRY

2. Aim #1 What is an organic compound and what are its properties ? Organic chemistry is the study of carbon and its compounds found in fossil fuels, plants, animals Examples include: gasoline, oil, sugars Hydrocarbon – contains only the elements H & C (TABLE Q) Therefore, hydrocarbons are organic, but not all organic compounds are hydrocarbons

3. Why is carbon so special? Has 4 valence electrons, so it can bond 4 times to achieve a stable octet

4. Nonelectrolytes (do not conduct electricity ) React slowly because they are covalent (nonmetal + nonmetal) Usually low melting point and boiling point Insoluble and immiscible in water PROPERTIES OF ORGANIC COMPOUNDS

5. Which of the following are organic? Which of the following are hydrocarbons?

6. Types of Chemical Formulas Molecular Formula - shows the # of atoms of each element in a compound (least informative formula) Ex. Propane = C 3 H 8

7. Types of Chemical Formulas Structural Formula- shows the number of atoms of each element AND the arrangement of the atoms ; most informative formula Ex. Propane =

8. Types of Chemical Formulas Condensed/Collapsed Formula- combination of both structural and molecular formulas -each carbon is written with its constituent hydrogens followed by the proper subscript Ex. Propane = CH 3 CH 2 CH 3

9. Structural Formula Condensed Formula     CH 3 C 2 CH 3

10. HOMOLOGOUS SERIES Table Q shows the general formulas and structures for 3 families of hydrocarbons

11. Alkanes- single bonded hydrocarbons contains ONLY (C-C) These bonds are considered saturated. They have the maximum number of hydrogens attached. Remember that each bond represents 1 pair of shared electrons (2 e- total per bond ) General formula: C n H 2n+2 Example: Methane

12. 2. Alkenes- double bonded hydrocarbons, contains (C=C) These bonds are considered unsaturated General formula: C n H 2n Example: Butene

13. 3. Alkynes – triple bonded hydrocarbons, contains (C- C triple bonds) These bonds are considered unsaturated General formula C n H 2n-2 Example: Propyne

14. How can we name hydrocarbons? -IUPAC To name simple hydrocarbons (straight chain, only C and H), we will put information from Table P and Table Q together Table P shows the prefix to determine how many carbons are in a compound Ex ) Give the prefixes for the following: C 2 H 6 C 4 H 6 C 5 H 12 C 7 H 14 C 8 H 18 C 10 H 20

15. How can we name hydrocarbons? -IUPAC Steps in naming simple (unbranched) hydrocarbons: How many carbon atoms are in the longest continuous chain ? Find the prefix for this from Table P . If it is an alkane , simply add the suffix “ - ane ” to the name.

16. How can we name hydrocarbons? -IUPAC 3. If it is an alkene , you must first indicate the location of the double bond (s) if the molecule has more than 3 Cs. Do this by numbering the carbons on the chain and stating the l owest carbon # where the double bond is located . Then add the suffix “ - ene ” to the name.

17. How can we name hydrocarbons? -IUPAC 4. If it is an alkyne , you must first indicate the location of the triple bond(s ) if the molecule has more than 3 Cs. Do this by numbering the carbons on the chain and stating the lowest carbon # where the triple bond is located. Then add the suffix “ - yne ” to the name.

18. Aim # 3 What are isomers? Isomers have the same molecular formula but are rearranged in a different structure with different chemical and physical properties . At least 4 carbons must be present in a molecule to have isomers Methane, ethane, and propane DO NOT have any isomers

19. What are isomers? Butane is the first molecule to have isomers. The larger the molecule (the more carbon atoms), the more isomers the molecule will have 3 ways to make an isomer: 1. Make a branch (on a non-terminal carbon) 2. Move a branch 3. Move a multiple bond (a double or triple bond)

20. What are isomers? Pentane Isomers

21. What are isomers? Pentene Isomers

22. Aim # 4 How can we name & draw substituted hydrocarbons? Count the longest parent chain of carbon atoms – name that chain Scan the chain and take note of anything that is not a C or H Indicate the lowest number carbon that has the substitution Name the substitution (F- fluoro , Cl- chloro , Br- bromo , I- iodo , CH 3 - methyl, CH 2 - ethyl) Notice that if there are more than one substitutions, you must indicate all of their locations (which # C they’re attached to), and put a numerical prefix in front of the substitution name (“ di- ” for 2, “ tri- ” for 3, “ tetra- ” for 4)

23. How can we name and draw substituted hydrocarbons? chloromethane

24. How can we name and draw substituted hydrocarbons? dichloromethane

25. How can we name and draw substituted hydrocarbons? F H   H - C – C – H H H 1-fluoroethane

26. How can we name and draw substituted hydrocarbons? 1,1 - difluoroethane

27. How can we name and draw substituted hydrocarbons? F H   H - C – C – H H F 1,2 - difluoroethane

28. How can we name and draw substituted hydrocarbons? 1- fluoro, 1,2 – dibromo ethane

29. How can we name and draw substituted hydrocarbons? 1,2 – dichloropropane

30. How can we name and draw substituted hydrocarbons? 1,3 - dicholoropropane

31. How can we name and draw substituted hydrocarbons? 2-methylpropane

32. How can we name and draw substituted hydrocarbons? 2,2 – dimethyl butane

33. How can we name and draw substituted hydrocarbons? 2, 2, 3 – trimethyl pentane

34. Aim # 5 What are functional groups? Although hydrocarbons are the most basic organic compounds, many other organic compounds form when other atoms replace one or more hydrogen atoms in a hydrocarbon These atoms or groups of atoms, called functional groups , replace hydrogen atoms in a hydrocarbon and give the compound distinctive physical and chemical properties The naming of these compounds is made easy because they derive their names from the hydrocarbon with the corresponding number of carbon atoms

35. Halides- Have one of the halogens as a branched group F ( fluoro ) Cl ( chloro ) Br ( bromo ) I ( iodo )

36. Fluoromethane 1, 2 dibromo ethane Chloromethane

37. Alcohols Have an –OH group F lammable, soluble NOT bases (covalently bonded) and NOT electrolytes Has the suffix “- ol ” and must also state the location of the –OH along the carbon chain (using lowest # location)

38. Organic Acids Have a carboxyl group (-COOH) at the last carbon Also known as carboxylic acids : weak acids/weak electrolytes because they generate H + ions in solution Has the suffix “- oic acid ”

39. Aldehydes CHO group found at the end of the hydrocarbon chain Soluble and reactive Has the suffix “-al ”

40. Ketones CO group located on an interior carbon atom Can NEVER be a terminal carbon, or it would be an aldehyde! Has the suffix “-one” Somewhat soluble, needs at least 3 carbons

41. Ester Contains COO connecting parent chain to branch Smell nice! Found in perfumes, foods Has the suffix - anoate

42. Amine Nitrogen is present Used in dyes , f ound in proteins, DNA Has the suffix - amine

43. Amide propanamide Contains Used in dyes Has the suffix - amide

44. Ether Dimethyl ether Methyl ethyl ether a) look for –O- somewhere in the middle b) anesthetic, soluble c) Name small chain, then the large chain and follow with suffix “- ether ”

45. Aromatic Hydrocarbons 6 carbons are in a closed ring with alternating double and single bonds b) Called benzene c) It is very stable d) Can be substituted Methylbenzene 1,4-dichloro benzene

46. Aim # 6 What are the different organic reactions?

47. 1. Combustion In the presence of oxygen: A hydrocarbon and oxygen produces CO 2 and water In limited oxygen: A hydrocarbon and oxygen produce CO and Water

48. 2. Substitution CH 4 + Cl 2  CH 3 Cl + HCl Involves a saturated hydrocarbon One or more H gets replaced by another atom or group Compare the number of H on the reactant and product side

49. 3. Addition Involves an unsaturated hydrocarbon, atoms/ groups are added in at a multiple bond site. Unsaturated hydrocarbon  saturated hydrocarbon b. Hint : look for 2 reactants and one product

50. 4. Esterification An organic acid and alcohol makes an ester and water Should be able to recognize the acid group and the hydroxyl group in the reactants Hint: table R to recognize the ester in the products

51. 5. Saponification A fat reacts with a base to produce and alcohol (look for glycerol) and a soap

52. Fermentation Glucose yields ethanol and CO 2

53. Polymerization 5CH 2 =CH 2 → ( CH 2 -CH 2 ) 5 Addition Polymerization: Unsaturated monomers join by breaking their double or triple bonds to bond with one another, making long chains Several monomers combine to make the polymer Condensation Polymerization: Creation of a polymer plus water as a product When an unsaturated hydrocarbon called a monomer (one unit), bonds itself in long chains creating a polymer (many units )