1. Chemistry-1 CP Chapters 22 & 23 Hydrocarbon Compounds

2. ORGANIC CHEMISTRY: The study of compounds containing CARBON
There are more than a 10 million organic compounds!

3. Allotropes
Lonsdaleite
One of two or more different molecular forms of the same element in the same physical state

4. HYDROCARBONS
HYDROCARBON PREFIXES
The simplest organic compounds that contain only carbon and hydrogen
Carbon has 4 valence electrons, and therefore always forms 4 covalent bonds!
Prefix
# of Carbons
Meth- 1
Eth- 2
Prop- 3
But- 4
Pent- 5
Hex- 6
Hept- 7
Oct- 8
Non- 9
Dec- 10

5. ILLUSTRATING HYDROCARBONS
C4H10
Molecular Formula
Complete Structural Formula
C-C-C-C
Carbon Skeleton
CH3(CH2)3CH3
Line-Angle Formula
Condensed Structural Formulas

6. Alkanes A hydrocarbon in which there are only single bonds
In an alkane all the carbon-carbon bonds are single covalent bonds
All other bonds are carbon-hydrogen bonds
The carbon atoms in an alkane can be arranged in a straight chain or in a chain that has branches.
Alkanes are called saturated compounds because they contain only single covalent bonds

7. Straight Chain Alkanes
Contain any number of carbon atoms, one after the other, in a chain
Homologous Series: A constant increment of change in molecular structure from one compound in the series to the next
In an alkane a CH2 group is the increment of change

8. Naming Straight-Chain Alkanes
Naming Alkanes
Drawing a Structural Formula
For all alkanes the name ends in -ane
Write the symbol for carbon as many times as necessary to get the proper chain length
Count the carbon atoms and add the appropriate prefix
Complete each carbons bonds with hydrogen
Name: C6H14
Draw the structural formula for octane.

9. Branched Chain Alkanes
An alkane with one or more alkyl groups
Substituent: An atom or group of atoms that can take the place of a hydrogen atom on a parent hydrocarbon molecule
Parent Alkane: The longest continuous carbon chain of a branched–chain hydrocarbon
Alkyl Group: A hydrocarbon substituent

10. NAMING BRANCHED ALKANES
EXAMPLE:
Find the largest chain of carbons in the molecule (the parent structure)
# the carbons in the main chain in sequence, starting so that the substituents will be on the carbons of the lowest possible numbers
Add numbers to the name of the substituent groups to identify their positions
Use prefixes to indicate the appearance of the same group more than once in the structural formula
List the names of the alkyl substituents in alphabetical order
Commas are used to separate #s. Hyphens to separate numbers and words. Entire name without spaces.

11. PROPERTIES OF ALKANES Molecules of hydrocarbons are nonpolar molecules
Attraction between nonpolar molecules are weak van der Waals forces
Alkanes of lower molar mass tend to be gases or liquids that boil at low temperatures
Will form a solution with nonpolar compounds because “Like dissolves Like”
Will not form solutions with polar compounds

12. UNSATURATED COMPOUNDS: Compounds that contain double or triple carbon-carbon bonds
Alkenes
Alkynes
Hydrocarbons that contain one or more carbon-carbon double-covalent bonds
Hydrocarbons that contain one or more carbon-carbon triple covalent bonds
Examples:

13. To Name Alkenes/Alkynes
Example
Find the longest chain in the molecule that contains the double/triple bond (parent chain). Name with the appropriate prefix and the ending –ene (for alkenes) or –yne (for an alkyne)
Number the chain so the carbon atoms with the double-triple bonds have the lowest numbers. Include the number in the name if there is more than one possible location for the double-triple bond.
Substituents are numbered and named as they are with alkanes

14. Draw the structural formulas for:
Propyne Propane Propene

15. ISOMERS Compounds that have the same molecular
formula but different molecular structures

16. Structural Isomers Compounds that have the same molecular
formulas but the atoms are joined in a different way
Structural isomers differ in physical properties such as melting/boiling points
Have different chemical reactivities

17. PROPERTIES Butane Structure Melting Point (C) -60 -217
Methylpropane
Butane
Structure
Melting Point (C)
-60
-217
Boiling Point (C) 30 31
Stability
Reactively stable. Extremely flammable
Highly flammable
The more highly branched the hydrocarbon, the lower the boiling point hydrocarbon

18. STEREOISOMERS Molecules in which the atoms are joined in the
same order, but the positions of the atoms in
space are different.
1) Geometric Isomers: Atoms are joined in the same order but differ in orientation around a double bond.
trans: Similar groups are on opposite sides of the double bond
cis: Similar groups are on the same side of the double bond

19. Which is cis and which is trans?

20. STEREOISOMERS
Optical Isomers: Differ in the way that four different groups are arranged around a central carbon atom.
Asymmetric Carbon: A carbon with 4 different atoms or groups attached

21. FUNCTIONAL GROUPS
Organic compounds can be classified according to their functional group.
Functional Group: A specific arrangment of atoms in an organic compound that is capable of characteristic chemical reactions
Organic compounds can be classified by their functional groups!

23. Halocarbons A class of organic compounds containing
covalently bonded fluorine, chlorine, bromine or
iodine.
Naming: The halogen groups are named as substituents

24. Halocarbons Properties: Weak van der Waals interactions called
dispersion forces
Forces increase with halogen substitution
More highly halogenated organic compounds have higher boiling points
Very few are found in nature

25. Halocarbons
1987 Montreal Protocol on Substances that Deplete the Ozone Layer and its Amendments, which have both high ozone depleting potentials (ODPs)

26. Alcohols An organic compound with an –OH group
Hydroxyl Group: The –OH functional group
“In many ways, prohibition was the catalyst for the first (and arguably biggest) large-scale Do-It-Yourself science movement in the nation's history”. Robert T. Gonzalez, BBC

27. Naming Alcohols
1) Drop the –e ending of the parent alkane name and add the ending –ol
2) Parent alkane is the longest continuous chain that includes the carbon attached to the hydroxyl group
3) If the hydroxyl group can occur at more than one position, its position is designated with the lowest possible number.
4) Alcohols containing 2, 3, or 4 –OH substituents are named diols, triols, and tetrols

28. Properties of Alcohols
Capable of intermolecular hydrogen bonding
Higher boiling points than alkanes & halocarbons containing comparable numbers
Alcohols up to 4 carbon atoms are soluble in water
Solubility with 4 carbons or more is much lower
Carbon chain is nonpolar (not attracted to water)…more carbons = more nonpolar parts to the molecule
Hydroxyl part is polar…that’s why small alcohols are soluble in water

29. Uses of Alcohols Common Name: Isopropyl Alcohol IUPAC Name:
Rubbing alcohol
Base for perfumes, creams & lotions
Common Name: Ethylene glycol
IUPAC Name:
Main ingredient in antifreeze
Soluble in water
Freezes at -17.4C
Common Name: Ethanol
IUPAC Name:
Alcoholic Beverages
A depressant
In industry: denatured alcohol

30. Aldehydes An organic compound in which the carbon of
the carbonyl group is always joined to at least
one hydrogen
Carbonyl Group: a CO group

31. Ketones An organic compound in which the carbon of
the carbonyl group is joined to two other
carbons

32. Naming Aldehydes & Ketones
Identify the longest hydrocarbon chain containing the functional group
2. For aldehydes, replace the –e of the hydrocarbon with –al
3. For ketones, replace the –e of the hydrocarbon with –one
4. If the functional group can occur at more than one place, designate its position with the lowest possible number.

33. Properties of Aldehydes & Ketones
Form weak hydrogen bonds between the carbonyl oxygen and the hydrogen atoms of water
Low molar mass compounds are soluble in water
Above 5 or 6 carbon atoms, solubility is low
Soluble in nonpolar solvents
Boiling points are lower than alcohols
Boiling points are higher than alkanes
Because of polar ends they can have polar-polar interactions
Typically liquids or solids at room temperature

34. Uses of Aldehydes & Ketones
High molar mass aldehydes & ketones have fragrant or penetrating odors
Aromatic aldehydes often used as flavoring agents
Almond odor (benzaldehyde) & Cinnamon odor (cinnamonaldehyde)
Formaldehyde (methanal)
Acetone (propanone)
Solvent for plastics, nail polish removers, etc.

35. Esters Contain a carbonyl group and an ether link
(C-O-C) to the carbonyl group

36. Properties of Esters Uses of Esters Pleasant, fruity odors
Give blueberries, pineapples, apples, pears, bananas and many other fruits their characteristic odors
Give many perfumes their fragrances

37. Polymers