Organic Chemistry

1. Organic Chemistry

2. What is organic chemistry • The scientific study of carbon based compounds, hydrocarbons, and their derivatives.

3. Organic Chemistry con’t • Including the study of structure, properties, composition, reactions and preparation of these carbon based compounds • these carbon based compounds can include other elements such as: Hydrogen, Nitrogen, oxygen

4. Compounds are? • The chemical union of two or more elements

5. General themes in Organic chemistry • Organic chemistry=Ochem • “ R”groups represent attached groups of atoms, such as Hydrocarbon side chains. • Hydrocarbon: compounds containing only Carbon and Hydrogen. Remember Carbon always have “4 bonding e-”

6. Homologous series • Organic compounds are members of homologous series similar to a family • To be part of a homologous series the members differ by a –CH2 group • For example Alkanes:

7. Homologous series con’t • Homologous series: • Show similar chemical reactivity. • Can be represented by same general formula • Show similar chemical properties • Show gradual changes in physical properties.

8. Types of hydrocarbons • Hydrocarbons are classified into two main groups • Aliphatics (alkanes, alkenes, alkynes) which contain branches but do not contain a benzene ring. • Aromatic hydrocarbons are a unique type of cyclic hydrocarbon that is derived from a benzene ring

9. Hydrocarbons have two types of carbon-carbon (C-C) bonding • Single bonds only=Saturated Hydrocarbons • contain only C-C single bonds throughout. • Every available electron sharing site is occupied (saturated) by hydrogen atoms • Double/triple bonds= Unsaturated hydrocarbons • contain at least one C-C double bond or triple bond. • This means that some electron sharing sites on the carbon atoms are occupied by other carbon atoms (not saturated with hydrogen atoms).

10. Formulas for organic compounds • There are 3 types: • 1. Empirical- simplest whole number ratio of the atoms it contains • ethane: C2H6CH3 • Ethanoic AcidCH3COOHC2H4O2CH2O • Glucose C6H12O6CH2O • doesn’t give a whole lot of detail so it is not often used.

11. Formulas for organic compounds • 2. Molecular Formulas • The actual number of atoms of each element present. • Ethane C2H6 • Ethanoic AcidC2H4O2 • GlucoseC6H12O6

12. Molecular Formula • It is a multiple of the empirical formula • (empirical formula)*n=molecular formula • Mr= relative molecular mass • Mr= (molecular mass of empirical formula ) • For ethane: • Empirical formula is CH3 and Mr=30 • Mr=(molecular mass )n • 30=(12+(3*1.01))n • 30=(15.03)n • n=2 • Therefore the molecular formula is (CH3)2 or C2H6

13. Structural formula • Structural Formula • There are three types of structural: • Full structural • Shows the bonds of every atom • As well as the angle • A 2D image • Condensed structural formula • Does not show bonds, but groups atoms together • The minimum amount of information • CH3CH3

14. Structural formula con’t • Structural Formula • Stereochemical • Attempts to show 3D image • By convention: a solid enlarging wedge the bond is coming out of the page • A dotted line is going into the page

15. Which type am i? Full structural Condensed Stereochemical Stereochemical Full structural

16. What is a hydrocarbon • A compound that contains only C and H • When naming it is important to find the longest unbranched carbon chain • First understand what the picture means 3 2 4 6 5 2 1 1 4 3 5 6 Carbons? 3 2 H 2 3 H H 5 H H H H H H H H 2 1 H H 4 3 6 2 H 2 Hydrogen?

17. PRACTICE • Find the longest UNBRANCHED Hydrocarbon chain

18. IUPAC=International union of Pure and Applied Chemistry

19. Name that Hydrocarbon! Hexane Butane propane ethane

20. Side chains • Side chains are elements or groups of elements attached to the hydrocarbon chain • Also called substituent groups. • Important when it comes to naming.

23. Functional Groups • Are specific groups of atoms within molecules that are responsible for characteristic chemical reactions. • For example: • Alcohols are characterized by their functional group—OH

24. Functional group 1- Alkanes • ALKANES (CnH2n+2) • Alkanes are aliphatic hydrocarbons • They have only carbon-carbon single bonds • this means they are saturated hydrocarbons) Carbon Hydrogen

25. Alkanes • Properties of Alkanes: • Boiling point are dependent on: • intermolecular forces primarily, like London dispersion forces. • molecular size and surface area of the structure • They do not conduct electricity [because they are molecular compounds] • Are nonpolar so they are not miscible in water • React with oxygen in combustion reactions

26. Naming (Nomenclature) for sidechains • 1. Find longest unbranched chain of Carbons and number the carbon atoms this is the “root” • 2. Based of the number of carbons find the IUPAC name=the suffix • 3. Located and identify any sidechains= the prefix • 4. Use the attached Carbon • To identity where the side group is located.

27. 5. If there is more than 1 of the same kind of branch, use prefixes di, tri, tetra etc. to indicate this. • Place branches in (alphabetical order) in the name • Use commas to separate #s, and "–" to separate letters from #s. • written as: • C# sidechain attached too-sidechainprefixrootofcarbonchain

28. Example Comma to separate the #s # of the alkyl group • 2,5-dimethylhexane Suffix Root # to identify position of branches Alkyl prefix

29. What does 5-dimethylhexane look like?

30. For example • 3-ethyloctane octane C 3 Ethyl

31. Alkenes- CnH2n • Are unsaturated hydrocarbons [i.e. Have at least one double bond] • – end with suffix “ene” • A # must be used to indicate the position of the double bond. Such as but-2-ene • The longest chain must contain the double bond • Physical properties very similar to the alkane

32. Alkenes- CnH2n- Con’t • tend to have fewer dispersion forces than alkanes, which allows them to be liquids at room temp, rather than solids • If there are two double bonds, then use the prefix “di” before the “ene”and indicate the placement of the double bonds with #’s, Three double bonds requires the prefix “tri” before the “ene”

33. Alkenes- CnH2n- Con’t • Chemical properties of Alkenes • Because of the strain at the location of the double bond, it is the reactive site of the molecule. • Undergo addition reactions to produce alkanes • H atoms tend to add on to the C atoms involved in the C-C double bond

34. ALKYNES( CnH2n-2) • Alkynes are also examples of unsaturated hydrocarbons. • They have at least one triple bond • Triple bonds are more reactive than double bonds • Alkyne names end with “yne”. Use a number to indicate the position of the triple bond. • Ethyne is the most common alkyne (also called acetylene)

35. Naming and drawing Alkenes and Alkynes • Identify the longest continuous chain which includes the double or triple bonds. • Identify the suffix which for alkenes is ``ene`` and for alkynes is ``yne.`` • The suffix must also include the location of the double or triple bonds. -2-yne • Number from the end that will give the location of the double or triple bond the lowest value.

36. Naming and drawing Alkenes and Alkynes • The location of the double or triple bond is indicated by the number of the carbon atom that precedes the bond. • Use a hyphen, a number, a hyphen and then the suffix “ene” or “yne” • Name the side or substituent groups same as done with alkanes.

37. EXAMPLE • 1. find the root- the longest chain of unbranched carbons that contains the double bond • 6 Carbon long • 2. identify the suffix- remember if it has a double bond the suffix ends with–ene • Hexene

38. 3. Number the carbons, so the double bond has the lowest number possible • Hex-1-ene • 4. identify the prefix- • One methyl on C-4, • One ethyl on C-4 • One methyl on C-5 • 4,ethyl-4,5-dimethyl

39. 4-ETHYL-4,5-DIMETHYLHEX-1-ENE The C# that the ethyl is attached too Indicates the number of the particular side chain C# that the double bond is attached too The C#s that the methyl is attached too #C in the longest chain on Cs Indicates double bond In alphabetical order the type of side chain or substituent groups attached

40. Think about a review game for the stuff we have gone overhave a few practice questions for the board ready as well

41. Cyclic Hydrocarbons • Alkanes, Alkenes and alkynes that are in rings • They have no beginning and no end

42. Naming and Drawing Hydrocarbons • Root: determine the number of carbon atoms in the ring (do not count those carbons that are part of a side group). The root name would coincide with this number, preceded by “cyclo” • Suffix: determine if the compound contains all single bonds, at least one double bond, or at least one triple bond. • The suffix will be“ane” “ene” or “yne” respectively. • There are no numbers used to indicate the location of the double or triple bond because it is assumed to be between carbons 1 and 2.

43. Prefix: Similar to naming the aliphatic hydrocarbons with a few extra things to consider: • atoms are not numbered: • if there are no side groups or only one side group • If more than one side group, number the C atoms to give you the lowest number in the name. • If double or triple bonds present in cyclic structure, ALWAYS number so C closest to these bonds is number one.

44. 6 1.Identify the root: 6 carbons=cyclohex 2.Idenitfy the suffix: double bond present =ene 3. Assign position numbers of C, so they go in the direction of the side group 4. Name the side group based off of the number of C atoms present 2=ethyl Name 4-ethylcyclohexene 1 5 4 2 3

45. 1.Identify the root: 6 carbons=cyclohex 2.Idenitfy the suffix: double bond present =ene 3.Assign position numbers 4. Name side groups one carbon=methyl 3 methyl sidegroups=trimethyl 5. Locations of side groups: 1,2,4 Name: 1,2,4-trimethylcyclohexene 6 1 5 2 4 3

46. More practice 1.Identify the root: 4 carbons=cyclobut 2.Idenitfy the suffix: triple bond present =yne 3.Assign position numbers 4. Name side groups one florine=floro 5. Locations of side groups: 1 Name: 1-florocyclobutyne 32 4 1 F

47. Organic Chemistry in Oil Sands • http://www.oilsands.alberta.ca/

48. Oil Sands fun! • In general to remember, • Oil sands are transported in hydrotransport pipelines to prevent sands from drying • Bitumen is separated out based on density, then is skimmed out • Bitumen is composed of 20% alkanes and 80% aromatic=OCHEM • Bitumen is separated into petroleum and other useful products • Through coking(removing C) and hydrocraking (adding H) petroleum is produced

49. Refining petroleum • The process of fractional distillation • 1. heat the petroleum • 2. the vapor rises up the fractional distillation tower and then gradually cools • 3. each Hydrocarbon component has a unique boiling point, so it condenses at different times • So different components can be removed at different times