1. Windsor University School of Medicine
Properties of alkanes & alkenes It is better to keep your mouth closed and be thought a fool than to open your mouth and remove all doubt.  Mark Twain
Ch.14 J.C. Rowe

2. Chain Length & the State of Matter of Organic Compounds
(# of carbons in the chain)
State of matter
1-4
gas
5-15
liquid
Greater than 15
solid

3. Prefix Names/Substituents
Prefix names & chain length
Some nonmetal substituents
Chain length
Prefix name 1
Meth- 2
Eth- 3
Prop- 4
But- 5
Pent- 6
Hex-
Element
or group
Name of group
(halide) -F
Fluoro-
-Cl
Chloro-
-Br
Bromo- -I
Iodo-
-NH2
Amino-

4. Structures : alkanes vs. alkenes
ALKANE (has single bonds)
ALKENE (has double bonds)

5. REACTIONS of ALKANES Combustion of alkanes Substitution of alkanes
Cracking of alkanes

6. Combustion of alkanes
You can burn them - destroying the whole molecule.
Complete combustion (given sufficient oxygen) of any hydrocarbon produces carbon dioxide and water.
Incomplete combustion (where there isn't enough oxygen present) can lead to the formation of carbon or carbon monoxide.

7. Substitution of alkanes
You can react them with some of the halogens, breaking carbon-hydrogen bonds.
Substitution reactions happen in which hydrogen atoms in the methane are replaced one at a time by chlorine atoms.
You end up with a mixture of chloromethane, dichloromethane, trichloromethane (chloroform) and tetrachloromethane (carbon tetrachloride).

8. Substitution reactions Cont’d.

9. Cracking of alkanes You can crack them, breaking carbon-carbon bonds
Cracking is the name given to breaking up large hydrocarbon molecules into smaller and more useful bits.
This is achieved by using high pressures and temperatures without a catalyst, or lower temperatures and pressures in the presence of a catalyst.

10. One possible reaction involving the hydrocarbon C15H32 might be:

11. Or, showing more clearly what happens to the various atoms and bonds:
The ethene and propene are important materials for making plastics or producing other organic chemicals. The octane is one of the molecules found in petrol (gasoline).

12. Cracking: catalytic vs. thermal
Catalytic cracking
Thermal cracking
The alkane is brought into contact with the catalyst at a temperature of about 500°C and moderately low pressures.
high temperatures(typically in the range of 450°C to 750°C) and pressures (up to about 70 atmospheres) are used to break the large hydro-carbons into smaller ones.
Thermal cracking gives mixtures of products containing high proportions of hydrocarbons with double bonds - alkenes

13. REACTIONS of ALKENES Combustion of alkenes Substitution of alkenes
Addition reactions :
Hydrogenation
Hydrohalogenation
Hydration
Polymerisation.

14. Combustion of alkenes
The alkenes are highly flammable and burn readily in air, forming carbon dioxide and water.
For example, ethene burns as follows :
C2H4 (g)+ 3 O2 (g) ==> 2 CO2 (g) + 2 H2O (g)

15. Substitution of alkenes
A substitution reaction involves replacings the hydrogen atoms of the alkene molecule with halogen atoms.
Note that the double bond does not break during this reaction.
Substitution reactions are rare for alkenes, therefore extreme conditions, such as high temperature & pressure &/or a catalyst, are needed to force the reaction.

16. Addition reactions of alkenes
Alkenes contain the unsaturated C=C
functional group which characteristically
undergo addition reactions. 
This is driven by the conversion of the weaker π bond into 2 new, stronger σ bonds.

17. Hydrogenation of Alkenes
Alkenes can be reduced to alkanes with H2 in the presence of metal catalysts such as Pt, Pd, Ni or Rh.
The two new C-H (sigma) σ bonds are formed simultaneously from H atoms absorbed into the metal surface.

18. Halogenation of Alkenes
overall transformation :  C=C to X-C-C-X
Reagent : normally the halogen (e.g. Br2) in an inert solvent like methylene chloride, CH2Cl2.

19. Reaction of Alkenes with Hydrogen Halides
When treated with HX alkenes form alkyl halides.
Hydrogen halide reactivity order : HI > HBr > HCl > HF (paralleling acidity order).

20. Hydration of Alkenes
When treated with aq. acid, most commonly H2SO4,  alkenes form alcohols.

21. Polymerisation of alkenes
During the polymerisation of ethene, thousands of ethene molecules join together to make poly(ethene) - commonly called polythene.
The number of molecules joining up is very variable, but is in the region of 2000 to

22. Naming alkanes/alkenes
See attached folders (5 worksheets)

23. unknown
Quality is never an accident. It is always the result of high intention, sincere effort and skillful execution. It represents the wise choice of many alternatives.