1. Prep-work
You are an analytical chemist working at GSK. You have been given two substances “A” and “B”. They both have the molecular formula: C4H10O. You have been told that one is primary alcohol and the other is a tertiary alcohol. Design an experiment to find distinguish the primary alcohol from the tertiary alcohol.

2. Combustion of alcohols
A. Draw out and state what kind of alcohol the following are:
Butan-1-ol
Butan-2-ol
2-methylbutan-2-ol
2,4-dimethylpentan-3-ol
4,4-dibromo-3-ethyl-2-5-dimethyl-hexan-1,3-diol
1,1,4-trichloro-2,3-diiodo-5-6-diethyloctan-1,4,6,8-tetraol
B. Write out the equation for the complete combustion of the first four alcohols

3. Combustion and oxidation of alcohols
L.O.:
Describe the combustion of alcohols.
Describe the oxidation of primary and secondary alcohols.
Outline the resistance to oxidation of tertiary alcohols

4. Aldehydes and ketones: Recap
What’s the difference between an aldehyde and a ketone?
Draw a 3 carbon and a 5 carbon aldehyde and name it.
Draw a a 3 carbon and a 5 carbon ketone and name it.

5. Oxidation recap ALWAYS 0!!! None Element Usual oxidation state
Exceptions
Elements joined to themselves, e.g. Cl2
ALWAYS 0!!!
None
Group 1 metals
always +1
Group 2 metals
always +2
Fluorine
always -1
Oxygen
usually -2
except in peroxides and F2O
Hydrogen
usually +1
except in metal hydrides where it is -1
Chlorine
usually -1
except in compounds with O or F

6. Oxidation of propan-1-ol to the aldehyde propanal

7. Oxidising carbon
More hydrogen bound to the carbon LOWERS (makes it more negative, or reduced) its oxidation number
More oxygen bound to the carbon RAISES (makes it more positive, or oxidised) its oxidation number

8. Oxidising alcohols Reaction conditions:
1. The oxidising agent is always acidified potassium dichromate written above the arrow like this:
K2Cr2O7/H2SO4
2. The reactants are the alcohol and “[O]” symbolising the oxidation agent
3. Heat is always needed

9. Potassium dichromate
In its oxidised state it is a bright orange liquid
What kind of bonds hold this compound together?

10. Oxidising primary alcohols
Write out the equation using displayed formula of the oxidation of ethanol to ethanal (water is also made)
(The reaction conditions require GENTLE HEAT with immediate distillation)

11. Aldehydes vs acid problem

12. Further oxidation of a primary alcohol
Using a process known as REFLUX, the reaction contents are continually heated at their boiling point temperature, so HOTTER and LONGER heating then alcohol conversion to an aldehyde
Still uses acidified potassium dichromate
Primary + Oxidising  Carboxylic + water
alcohol agent acid

14. Reflux apperatus Clamp stand
Cooling tube (tap water goes in at the top and out at the bottom continuously)
Reaction container
Heat source

15. Draw out the conversation of ethanol to ethanoic acid using the displayed formula

17. Oxidation of secondary alcohols
Like primary alcohols, also require acidified potassium dichromate and heat (but not reflux)
Converts the alcohol into a ketone
Write out, using displayed formula, the oxidation of hexan-2-ol to hexa-2-one

18. Oxidation of tertiary alcohols
The carbon attaching to the OH doesn’t have any hydrogens attached to it, so these can’t be oxidised.

19. Starter
Using [O] to represent the oxidising agent write the equations for the full oxidation of:
butan-1-ol
butan-2-ol
butan-1,2-diol
Extension: what do oxidation, respiration and combustion have in common? What are the differences?

20. Esterification and dehydration of alcohols
L.O.:
Describe the esterification of alcohols with carboxylic acids.
Describe elimination of H2O from alcohols to form alkenes.

21. The esterification reaction between propanoic acid and methanol

22. Naming esters
The alcohol becomes the alkyl group, the carboxylic acid becomes the alkanOATE part
e.g. ethanol and methanoic acid form ethyl methanoate

23. Diagram to show the bonds broken during esterification

24. Simple laboratory preparation of an ester

25. Sweet-smelling esters

26. Write out your own esterification reaction between methanol and methanoic acid using displayed formula
Now draw out the reaction between:
Ethanol and ethanoic acid
3,3-dichloro-2-methylhexanoic acid and butan-1-ol
Propanoic acid and hexan-3-ol

27. Draw these esters and name the alcohols and the carboxylic acids that made them:
The smell of oranges is from the ester:
1. Octyl ethanoate
Banana is made from:
2. Pentyl ethanoate

28. Dehydration of ethanol to form ethene

29. Dehydration of cyclohexanol to form cyclohexene