1. Organic Chemistry CE 541

2. Basic Concepts from Organic Chemistry Elements Elements “All organic compounds contain CARBON in combination to one or more elements”

3. Properties (compared to inorganics) usually combustible usually combustible generally have lower melting and boiling points generally have lower melting and boiling points less soluble in water less soluble in water existence of isomers existence of isomers slow reactions slow reactions have high molecular weight have high molecular weight most of organic compounds can serve as a food for bacteria most of organic compounds can serve as a food for bacteria

4. Sources of Organic Compounds Nature: sugars, starch, vegetable oils, animal oils Nature: sugars, starch, vegetable oils, animal oils Synthetic: manufacturing processes Synthetic: manufacturing processes Fermentation: Alcohols, anti-biotics, and acids which are derived by the action of microorganisms upon organic matter. Fermentation: Alcohols, anti-biotics, and acids which are derived by the action of microorganisms upon organic matter.

5. The Carbon Atom Why many compounds of carbon? carbon atom has four electrons to share carbon atom has four electrons to share ability of carbon atoms to link together in a wide variety of ways: ability of carbon atoms to link together in a wide variety of ways: Continuous Open Chain Continuous Open Chain

6. Chain with Branches Chain with Branches In a Ring In a Ring

7. Chain or Ring Containing Other Elements Chain or Ring Containing Other Elements

8. The structural formula of organic compound may be simplified, for example: Can be written as: CH 3 -CH 2 -CH 2 OH Or simply as: CH 3 CH 2 CH 2 OH

9. Isomerism Isomers “are compounds that contain the same number of the same atoms in different arrangements” Examples Examples (1) (1)

10. (2)(3)(4) Each of the four compounds has its own physical and chemical properties

11. Hydrocarbons “Are organic compounds that contain only Carbon and Hydrogen elements”. The simplest hydrocarbon is methane (CH 4 ). Methane is composed of four (4) hydrogen atoms and one carbon atom Hydrogen has one valence electron Hydrogen has one valence electron Carbon has four valence electron Carbon has four valence electron CH 4  CondensedExpanded StructuralStructural FormulaFormula

12. Classification of the Hydrocarbon Hydrocarbons Aliphatic Hydrocarbon AlkanesAlkenesAlkynes Aromatic Hydrocarbon

13. Aliphatic Hydrocarbons Two Types (1) Saturated “Those in which adjacent carbon atoms are joined by a single bond”

14. (2) Unsaturated “Those in which adjacent carbon atoms are joined by more than one bond (at least two of the carbon atoms)”

15. Alkanes (Saturated) “are also known as paraffins”. Their general molecular formula is: C n H 2n+2 (for open chain) Hexane (6 C and 14 H)

16. C n H 2n (for cycloalkanes) Cyclohexane (6 C and 12 H)

17. The simplest alkane compound is methane (CH 4 ). Methane is: gas gas highly explosive highly explosive greenhouse gas greenhouse gas

18. The First Ten Continuous-Chain Alkanes Molecular FormulaStructural FormulaIUPAC Namen CH 4 CH 4 Methane1 C 2 H 6 CH 3 -CH 3 Ethane2 C 3 H 8 CH 3 -CH 2 -CH 3 Propane3 C 4 H 10 CH 3 -(CH 2 ) 2 -CH 3 Butane4 C 5 H 12 CH 3 -(CH 2 ) 3 -CH 3 Pentane5 C 6 H 14 CH 3 -(CH 2 ) 4 -CH 3 Hexane6 C 7 H 16 CH 3 -(CH 2 ) 5 -CH 3 Heptane7 C 8 H 18 CH 3 -(CH 2 ) 6 -CH 3 Octane8 C 9 H 20 CH 3 -(CH 2 ) 7 -CH 3 Nonane9 C 10 H 22 CH 3 -(CH 2 ) 8 -CH 3 Decane10

20. Butane has two isomers n-butane isobutane (2 methylpropane)

21. Pentane has three isomers Pentane isopentane (2-methylbutane) Neopentane (2,2-dimethylpropane)

22. As the number of carbon atoms in alkanes was increased, the number of constitutional isomers will also increase: hexane has 5 isomers hexane has 5 isomers heptane has 9 isomers heptane has 9 isomers octane has 18 isomers octane has 18 isomers nonane has 35 isomers nonane has 35 isomers decane has 75 isomers decane has 75 isomers

23. How to draw constitutional isomers? Take hexane (C 6 H 14 ) as an example (hexane has 5 isomers) Draw a carbon skeleton (no hydrogen atoms) using all of carbon in a continuous chain. Remove one carbon atom from the end of the chain and place it on another carbon atom so that the new skeleton differs from the previous carbon skeleton. Repeat this procedure until you exhaust all possibilities of relocating one carbon atom

24. If carbon atom was place on one of the end atoms This is similar to the skeleton shown above

25. Next, if necessary, remove two carbon atoms from the continuous chain skeleton in (1) and relocate them either as single carbon atoms or as a two carbon fragment on other atoms in the chain. Write all possible different skeletons. Continue this procedure, if needed, for three carbon atoms, till you have the number of constitutional isomers as given in the problem. Check all skeletons to be sure that they are all different.

26. Place hydrogen atoms on the carbon atoms in each skeleton, remembering that there are four (4) bonds to each carbon atom. The 5 isomers are: CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3 CH 3 -CH-CH 2 -CH 2 -CH 3 CH 3 CH 3 CH 3 -CH 2 -CH-CH 2 -CH 3 CH 3 CH 3 CH 3 -C-CH 2 -CH 3 CH 3 CH 3 CH 3 -CH-CH-CH 3 CH 3 CH 3 CH 3 CH 3

27. Physical Properties of Alkanes (Table 5-1) colorless colorless odorless odorless quite soluble in water (especially those having 5 carbon atoms or more) quite soluble in water (especially those having 5 carbon atoms or more) dissolve in many solvents dissolve in many solvents at room temperature at room temperature C 1 to C 5 are gaseous C 1 to C 5 are gaseous C 6 to C 17 are liquids C 6 to C 17 are liquids C 18 and above are solids C 18 and above are solids

28. Homologous Series When series of compounds differ by a common increment (such as CH 2 in the case of alkanes), the series is referred to as being homologous series. In such cases, a general formula can be established to express the compounds (in this case C n H 2n+2 )

29. Radicals When one hydrogen atom is dropped from the methane- series hydrocarbon, the –ane ending is dropped and a –yl is added MethanCH 4  CH 3 -methyl EthaneC 2 H 6  C 2 H 5 - ethyl

30. Nomenclature First consider the nomenclature of the Alkyl groups. Alkyl groups are derived by removal of one hydrogen atom from an alkane. Alkyl groups are named by replacing the –ane ending of the alkane (methane) by –yl (methyl) in the case of simpler hydrocarbons.

31. Methane CH 4  CH 3 - Methyl EthaneCH 3 CH 3  CH 3 CH 2 - Ethyl PropaneCH 3 CH 2 CH 3  CH 3 CH 2 CH 2 - Propyl ButaneCH 3 CH 2 CH 2 CH 3  CH 3 CH 2 CH 2 CH 2 - Butyl PentaneCH 3 CH 2 CH 2 CH 2 CH 3  CH 3 CH 2 CH 2 CH 2 CH 2 - Pentyl HexaneCH 3 CH 2 CH 2 CH 2 CH 2 CH 3  CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 - Hexyl

32. Simple Alkyl Groups and their Names The most common alkyl groups will be discussed.

33. Methyl Group Methane has one carbon and four hydrogen atoms. The methyl group also has one carbon but only three hydrogens. In place of the fourth hydrogen, there is a bond to something else. methyl H | H-C- | H H | H-C- | H

34. Ethyl Group Ethane has two carbons and six hydrogen atoms. If any one of those hydrogens is removed and replaced with a bond to something else, you end up with an ethyl group. ethyl H H | | H-C-C- | | H H H H | | H-C-C- | | H H

35. Propyl Groups Propane has three carbons and eight hydrogen atoms. If one of the six end hydrogens is replaced by a bond to something else, you end up with a normal propyl group. If one of the two middle hydrogens is replaced by a bond to something else, you end up with an isopropyl group. n-propyl or simply propyl H H H | | | H-C-C-C- | | | H H H H H H | | | H-C-C-C- | | | H H H isopropyl H H H | | | H-C-C-C-H | | | H H H H H | | | H-C-C-C-H | | | H H

37. Butyl Groups The next set of alkyl groups contains four carbons. That is why they are called butyl groups. There are four types of butyl groups each with a different combination of carbon chain and bonding point.

38. Other Alkyl Groups

40. The IUPAC (International Union of Pure and Applied Chemistry) name for Alkanes are obtained using the following rules: 1. All alkanes have the ending – ane 2. The longest continuous chain of carbon atoms is determined, and this chain is used as the parent structure. The parent structure is pentane. If the chain is in the form of a ring, then the prefix cyclo- is used.

41. 3. The carbon atoms in this chain are numbered by starting at the end that would give the lowest numbers to the group or groups attached to the parent structure. In the above example, the lowest numbers would be obtained by numbering from the left side (2 and 3 are lower than 3 and 4) 4. The group attached to parent structure, other than hydrogen, is given both name and number. Halogens attached to the parent structure are named ( halo— ) Clis chloro Brisbromo Iisiodo NO 2 isnitor Alkyl groups are given their IUPAC names

42. 5. If more than one of the same group appears as a substitute in a given molecule, then the prefixes di, tri, tetra, and penta are used to indicate the number of times this group appears (two, three, four, and five times) The position of these groups on the numbered parent structure is indicated in increasing numerical order. Each group must have a number to indicate its position on the parent structure

43. Since 2 methyl groups are attached to the parent structure and hence di is used (dimethyl). The groups are attached at the 2nd and 3rd positions, so we use (2,3-dimethyl). The comma (, ) is used between numbers and the hyphen ( - ) is used between numbers and names. 6. If more than one type of group is attached to the parent structure, these groups are placed in alphabetical order in the name of the compound. di -, tri -, tetra -, sec -, tert – are ignored in determining the order The underlined letter is used to determine the alphabetical order in the following list of groups dichloro, trimethyl, isopropyl, sec-butyl, tert-butyl, tetraethyl

44. Examples Name the following compounds using IUPAC names

46. Chemical Reactions

47. Alkenes (Olefins) They are aliphatic hydrocarbons that have the general molecular formula CnH2n for open-chain systems The simplest alkene is the Ethylene (C 2 H 4 ) The simplest alkene is the Ethylene (C 2 H 4 ) Alkenes are unsaturated hydrocarbons, since they contain fewer than the maximum number of hydrogen atoms in their general formula Alkenes are unsaturated hydrocarbons, since they contain fewer than the maximum number of hydrogen atoms in their general formula Alkenes contain a double bond Alkenes contain a double bond

48. Ethylene (ethene)

49. The First Alkenes Are

50. Nomenclature

52. Examples

54. Alkynes (Acetylene Series) Alkynes (Acetylene Series)

55. Nomenclature 1. All have the ending –yne (IUPAC name of acetylene is enthyne) 2. The logest continuous chain of carbon atoms that contain the triple bond is used as the parent structure 3. The chain is numbered such that the triple bond has the lowest possible number 4. The position of the triple bond is indicated by placing the lowest number of the carbon atom of the triple bond before the name of the parent structure 5. the groups attached to the parent structure, other than hydrogen, are given both name and number and are placed in alphabetical order.

56. Examples

58. Chemical Reactions