1. Organic Compounds
- Alcohols -

2. Common Alcohol Compounds
Ethanol
Adult beverages and Biofuel
Menthol
TigerBalm, Vicks Vaporub
Listerine (menthol and ethanol)
Ethylene glycol
Car antifreeze
Cholesterol

3. Alcohol Properties
Members of the alcohol family contain a hydroxyl (-OH) group making them polar molecules
The –OH is capable of hydrogen bonding (the strongest of intermolecular forces)
Presence of –OH causes an increase in attractive forces between molecules in comparison to hydrocarbon chains of equal size
e.g Ethanol b.p. 78 ºC Ethane b.p. -89 ºC

4. Short chained alcohols dissolve completely in water
Longer chained alcohols dissolve well in non- polar solutions because of their long hydrocarbon tails (phospholipids)
Three types of alcohols
alcohols are sub-classified according to the type of carbon to which the –OH group is attached

5. Primary (1°) Alcohol
An alcohol in which the hydroxyl functional group is attached to a carbon which is itself attached to only one other carbon atom

6. Secondary (2°) Alcohol
An alcohol in which the hydroxyl functional group is attached to a carbon which is itself attached to only two other carbon atom

7. Tertiary (3°) Alcohol
An alcohol in which the hydroxyl functional group is attached to a carbon which is itself attached to only three other carbon atom

8. IUPAC Naming of Alcohols
Locate the longest chain that contains an – OH group attached to one of the carbon atoms. Name the parent alkane.
NOTE: Cyclic alcohols. An –OH (hydroxyl) group can be attached to a cyclic hydrocarbon and may be considered attached to the parent chain.
Replace the –e at the end of the name of the parent alkane with –ol.

9. Add a position number before the root of the name to indicate the location of the –OH group. (Remember to number the main chain of the hydrocarbon so that the hydroxyl group has the lowest possible position number.)
NOTE: If there is more than one –OH group, leave the –e in the name of the parent alkane, and put the appropriate preix (di-, tri-, or tetra-) before the suffix –ol)

10. Name the number of any other branches on the main chain
Name the number of any other branches on the main chain. Add the name of these branches to the prefix.
Put the name together:
prefix + root + suffix

11. Naming Alcohols Practice
1,3-butadiol
2-methyl-2-propanol
1,2,3-propatriol
2-propanol

12. Naming Alcohols Practice
phenol
2,3-dimethylphenol

13. Four Common Reactions Involving Alcohols
Addition (hydration)
Oxidation (combustion)
Substitution
Elimination (dehydration)

14. 1) Addition (hydration)
Preparing alcohols from alkenes
Hydration: addition reaction with water
An acid is needed as a catalyst (H2SO4(aq))
Must follow Markovnikov’s Rule
General Equation:
Specific Example:

15. 2) Oxidation (combustion)
Alcohols undergo complete combustion to produce carbon dioxide and water
Specific Example:

16. CH3 – CH2 – OH + HCl  CH3 – CH2 – Cl + H2O
3) Substitution
Preparing alkyl halides from alcohols
Substitute a halogen for a hydroxyl group
Aqueous acids (HCl, HBr, HF and HI) are needed
Specific Example:
CH3 – CH2 – OH + HCl  CH3 – CH2 – Cl + H2O

17. 4) Elimination (dehydration)
Preparing alkenes from alcohols
Results in the removal of water
Requires a catalyst (concentrated H2SO4)
NOTE: The opposite reaction would be a hydration
General Equation:
Specific Example:

18. Learning Checkpoint Assigned Questions: p.41 #1,2,3 (naming)
p.42 #4,5 (properties) p.44 #7,8,9
Worksheet - Reactions and Functional Groups (Alkenes and Alcohols)
Read “Driving your car on ethanol article” and answer questions from the article