1. Combustion of alcohols A.Draw out and state what kind of alcohol the following are: 1.Butan-1-ol 2.Butan-2-ol 3.2-methylbutan-2-ol 4.2,4-dimethylpentan-3-ol 5.4,4-dibromo-3-ethyl-2-5-dimethyl-hexan-1,3-diol 6.1,1,4-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

2. 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

3. Aldehydes and ketones: Recap 1.What’s the difference between an aldehyde and a ketone? 2.Draw a 3 carbon and a 5 carbon aldehyde and name it. 3.Draw a a 3 carbon and a 5 carbon ketone and name it.

4. Oxidation recap Element Usual oxidation state Exceptions Elements joined to themselves, e.g. Cl 2 ALWAYS 0!!!None Group 1 metalsalways +1 Group 2 metalsalways +2 Fluorinealways -1 Oxygenusually -2 except in peroxides and F 2 O Hydrogenusually +1 except in metal hydrides where it is -1 Chlorineusually -1 except in compounds with O or F

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

6. 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

7. Oxidising alcohols Reaction conditions: 1.The oxidising agent is always acidified potassium dichromate written above the arrow like this: K 2 Cr 2 O 7 /H 2 SO 4 2.The reactants are the alcohol and “[O]” symbolising the oxidation agent 3. Heat is always needed

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

9. 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)

10. Aldehydes vs acid problem

11. 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

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

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

16. 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

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

18. Esterefication and dehydration of alcohols L.O.:  Describe the esterification of alcohols with carboxylic acids.  Describe elimination of H 2 O from alcohols to form alkenes.

19. The esterification reaction between propanoic acid and methanol

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

21. Diagram to show the bonds broken during esterification

22. Simple laboratory preparation of an ester

23. Sweet-smelling esters

24. Write out your own esterification reaction between methanol and methanoic acid using displayed formula Now draw out the reaction between: 1.Ethanol and ethanoic acid 2.3,3-dichloro-2-methylhexanoic acid and butan- 1-ol 3.Propanoic acid and hexan-3-o

25. 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

26. Dehydration of ethanol to form ethene

27. Dehydration of cyclohexanol to form cyclohexene