1. Chapter 22
Hydrocarbons

2. Alkanes Organic Compounds Vitalism
Discovered by 19th century scientists
They observed that living things produce an immense (large) amount of carbon compounds
Vitalism
Belief held by 19th century scientists
Organisms possessed a mysterious “vital force” that enabled them to assemble carbon compounds. These would never be able to be created in a laboratory
This was one of the reasons the 19th century scientists were unable to synthesize organic compounds in the lab

3. Alkanes Disproving Vitalism
Friedrich Wohler started disproving vitalism
He created urea in a lab
Led to a slew of other experiments by European Chemists
They disproved vitalism
Organic Compound: Applies to all carbon-containing compounds with the main exceptions being carbon oxides, carbides, and carbonates. These exceptions are considered inorganic.

4. Hydrocarbons
Hydrocarbons: Contain only the elements carbon and hydrogen.
There are thousands of different types of arrangements that can be made out of carbon and hydrogen.
Four different ways of displaying the hydrocarbons:
Molecular Formula
Structural Formula
Ball-and-Stick Model
Space-filling Model

6. Straight-Chain Alkanes
Alkanes: Hydrocarbons that have only single bonds between atoms.
Homologous Series: A series of compounds that differ from one another by a repeating unit
Name
Structural Formula
Methane
CH4
Ethane
C2H6
Propane
C3H8
Butane
C4H10
Pentane
C5H12
Hexane
C6H14
Heptane
C7H16
Octane
C8H18
Nonane
C9H20
Decane
C10H22
_____ane
C(X)H((X*2)+2)

8. Branched-Chain Alkanes
Might have the same molecular formula as straight chain alkyls, but they are not in a straight line. Instead, their carbon and hydrogens “branch”.
They have different chemical and physical properties.

9. Naming Branched-Chain Alkane
Parent Chain: Longest continuous chain of carbon atoms
Substituent Groups: All side branches, as they appear to substitute for a hydrogen atom in the straight chain
How to represent the ending:
Straight-Chain Alkane: -ane
Branched-Chain Alkane -yl

10. Naming Branched-Chain Alkanes
Name
Structural Formula
Methyl
CH3-
Ethyl
C2H5-
Propyl
C3H7-
Butyl
C4H9-
Pentyl
C5H11-
Hexyl
C6H13-
Heptyl
C7H15-
Octyl
C8H17-
Nonyl
C9H19-
Decyl
C10H21-

11. Naming Branched-Chain Alkanes
Name
Structural Formula
Methyl
CH3-
Ethyl
C2H5-
Propyl
C3H7-
Butyl
C4H9-
Pentyl
C5H11-
Hexyl
C6H13-
Heptyl
C7H15-
Octyl
C8H17-
Nonyl
C9H19-
Decyl
C10H21-

12. Naming Branched-Chain Alkanes
Count the number of carbons in the longest continuous chain.
Use the name of the straight-chain alkane with that number as the name of the parent chain of the structure.
Number each carbon in the parent chain
Locate the end carbon closest to the substituent group. Label that carbon (1). This ensures that the substituent groups are given the lowest number possible.
Name each alkyl group substituent
The names of these groups are placed before the parent chain
If the same alkyl group occurs more than once as a branch on the parent structure, use a prefix (di-, tri-, tetra-, etc)., before its name to indicate how many times it appears.
Whenever different alkyl groups are attached to the same parent structure, place their names in alphabetical order. Do not consider prefixes when determining alphabetical order.
Write the entire name using hyphens to separate numbers from words and commas to separate numbers.
Make sure to write the number placements before the substituent groups or to place the double-triple bonds.

14. 5-Ethyl-3-MethylOctane

15. Cyclic Alkanes and Alkane Properties
Cyclic Hydrocarbon: A hydrocarbon that contains a hydrocarbon ring
Cycloalkanes: A cyclic Hydrocarbon that only contains single bonds (Note, the name ALKANE)

16. Cyclic Hydrocarbons Basic Naming
Name
Structural Formula
Cyclopropane
C3H6
Cyclobutane
C4H8
Cylcopentane
C5H10
Cylcohexane
C6H12
Cycloheptane
C7H14
Cyclooctane
C8H16
Cyclononane
C9H18
Cyclodecane
C10H20
Cyclo_____ane
C(X)H((X*2)

17. Naming Cyclic Hydrocarbons
The ring is considered the longest chain of carbons. Name the rings according to cylcic hydrocarbon rules.
Number each carbon in the parent chain
Locate the end carbon closest to the substituent group. Label that carbon (1). This ensures that the substituent groups are given the lowest number possible. If only one substituent group, no numbering is necessary
Name each alkyl group substituent
The names of these groups are placed before the parent chain
If the same alkyl group occurs more than once as a branch on the parent structure, use a prefix (di-, tri-, tetra-, etc)., before its name to indicate how many times it appears.
Whenever different alkyl groups are attached to the same parent structure, place their names in alphabetical order. Do not consider prefixes when determining alphabetical order.
Write the entire name using hyphens to separate numbers from words and commas to separate numbers.
Make sure to write the number placements before the substituent groups or to place the double-triple bonds.

19. Properties of Alkanes Non-Polar Molecules
Do not form hydrogen bonds with each other
Hydrophobic
Low reactivity

20. Multiple Carbon-Carbon Bonds
Saturated Hydrocarbon: A hydrocarbon having only single bonds (alkane)
Unsaturated Hydrocarbon: A hydrocarbon that has at least one double or triple bond between carbon atoms.

21. Alkenes and Alkynes
Alkenes: An unsaturated hydrocarbon that has one or more double bonds
Alkynes: An unsaturated hydrocarbon that has one or more triple bonds

23. Basic Alkene Naming Name Structural Formula Ethene C2H4 Propene C3H6
Butene
C4H8
Pentene
C5H10
Hexene
C6H12
Heptene
C7H14
Octene
C8H16
Nonene
C9H18
Decene
C10H20
_____ene
C(X)H(X*2)

24. Naming Branched-Chain Alkenes
Count the number of carbons in the longest continuous chain.
Use the name of the straight-chain alkene with that number as the name of the parent chain of the structure.
Count the number of double/triple bonds and put the proper numeric prefix in front of the alkene name.
Number each carbon in the parent chain
Locate the end closest to the double/triple bond. Label that carbon (1). This ensures that carbons with the bonds are the lowest numbers.
Name each alkyl group substituent
The names of these groups are placed before the parent chain
If the same alkyl group occurs more than once as a branch on the parent structure, use a prefix (di-, tri-, tetra-, etc)., before its name to indicate how many times it appears.
Whenever different alkyl groups are attached to the same parent structure, place their names in alphabetical order. Do not consider prefixes when determining alphabetical order.
Write the entire name using hyphens to separate numbers from words and commas to separate numbers.
Make sure to write the number placements before the substituent groups or to place the double-triple bonds.

25. Properties of Alkenes Non-Polar Molecules
Do not form hydrogen bonds with each other
Hydrophobic
Higher reactivity than Alkanes
Helps fruit to ripen naturally (ethene)
Some natural scents are produced by Alkenes

27. Basic Alkyne Naming Name Structural Formula Ethyne C2H2 Propyne C3H4
Butyne
C4H6
Pentyne
C5H8
Hexyne
C6H10
Heptyne
C7H12
Octyne
C8H14
Nonyne
C9H16
Decyne
C10H18
_____yne
C(X)H((X*2)-2)

28. Naming Branched-Chain Alkenes
Count the number of carbons in the longest continuous chain.
Use the name of the alkyne with that number as the name of the parent chain of the structure.
Count the number of double/triple bonds and put the proper numeric prefix in front of the alkyne name.
Number each carbon in the parent chain
Locate the end closest to the double/triple bond. Label that carbon (1). This ensures that carbons with the bonds are the lowest numbers.
Name each alkyl group substituent
The names of these groups are placed before the parent chain
If the same alkyl group occurs more than once as a branch on the parent structure, use a prefix (di-, tri-, tetra-, etc)., before its name to indicate how many times it appears.
Whenever different alkyl groups are attached to the same parent structure, place their names in alphabetical order. Do not consider prefixes when determining alphabetical order.
Write the entire name using hyphens to separate numbers from words and commas to separate numbers.
Make sure to write the number placements before the substituent groups or to place the double-triple bonds.

29. Properties of Alkynes Non-Polar Molecules
Do not form hydrogen bonds with each other
Hydrophobic
Higher reactivity than Alkenes

30. Isomers
Isomers: Two ore more compounds that have the same molecular formula but different molecular structures

31. Structural Isomers Structural Isomers
Same molecular formula, but the atoms are bonded in a different order
Each isomer will have different chemical and physical properties

32. Stereoisomers Stereoisomers Geometric isomers
Same molecular formula, the atoms are bonded in the same order but are arranged differently within space
Each isomer will have different chemical and physical properties
Geometric isomers
Result from different arrangements of atoms around a double bond
Trans Form – Opposite Sides
Cis Form – Adjacent Form

34. Chirality Mirror Image Isomers Dextro- (D-isomer) = to the right
Levo – (L-isomer) = to the left

35. Optical Isomers
Asymmetric Isomers: A carbon atom that has four different atoms or groups of atoms attached to it.
Optical Isomer: Isomers that result from the different arrangement of the four groups around the same carbon atom (Mirror-Image Isomer)
Majority of optical isomers have the same chemical and physical properties, except when chirality is important

36. Optical Rotation
Optical Isomers are called Mirror-Image isomers, due to the way they affect light passing through them
Polarized Light: light that is filtered or reflected in such a way that all light waves lie in the same plane
Optical Rotation: when light passing through the L- and D- isomers get rotated clockwise (L) and counterclockwise (D)