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
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
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

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 1 2 1 4 3 5 6
Carbons? 3 2 H 2 3 H H 5 H H H H H H H H 1 2 3 H H 4 2 6 H 2
Hydrogen?

17. PRACTICE
Find the longest UNBRANCHED Hydrocarbon chain

18. IUPAC=International union of Pure and Applied Chemistry
# of Carbon
IUPAC Name
Example 1
Meth-
CH4-methane 2
Eth-
C2H6-ethane 3
Prop-
C3H8-propane 4
But-
C4H10-Butane 5
Pent-
C5H12-pentane 6
Hex-
C6H14-hexane

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.

21. Side chain/Substituent group
IUPAC prefix name
example
-CH3
Methyl
CH3CH(CH3)CH Methylpropane
-C2H5
Ethyl
CH(C2H5) Ethylpentane

22. Side chain/Substituent group
IUPAC prefix name
example
-C3H7
Propyl
CH(C3H7) propylheptane
-F,-Cl,-Br,-I
Fluoro, chloro, bromo,iodo
CCl4 tetrachloromethane

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. Place branches in (alphabetical order) in the name
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. 2,5-dimethylhexane Example Comma to separate the #s
# of the alkyl group
Suffix
2,5-dimethylhexane
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
4-ETHYL-4,5-DIMETHYLHEX-1-ENE
#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 over have 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. 6 1 5 2 4 3 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 3

46. F More practice 4 1 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 F

47. Organic Chemistry in Oil Sands

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

51. Structural Isomers
Structural isomers: have the same molecular formula but different structures.
Because of different structures, different physical properties exist as well
As the number of carbon atoms increase the number of possible isomers also increases
Pentane (C5H10)= 3 Isomers
Hexanes (C6H14)= 5 Isomers
Heptane (C7H16)= 9 Isomers
Nonane (C9H20)=35 Isomers

52. FOR example
C5H12

53. Homologous Series REMEMBER**
Members in a Homologous series differ by a mthylene group (CH2)
Homologous series can be thought of as families
The mp. and bp. increase as the number of C atoms increase because there is an difference in strength of the LD forces (or van der Waal’s forces)
The mp. and bp. also differ in some cases depending on polarity or hydrogen bonding.

54. Organics in General
Most organic compounds are non-polar and therefore insoluable in water(polar)
** Like dissolves like**
Solubility decreases as chain length increases
If an organic compound contains a functional group, it may allow it to hydrogen bond with water, and relatively water soluble

55. Aromatic Hydrocarbons