1. Organic Chemistry CARBON RULES OK
SCH3U/4U/4C
Mr. Bauernschmitt
General Panet HS

2. Why Carbon ? Group IV 4 stable covalent bonds
Readily forms long chain structures such as those in fats and oil.
make ethane
Carbon is very important carbon is the root of all life and we are called organisms because we are made from organic chemistry
Carbon is very special it performs catenation – repeatedly bonds to itself
Makes 4 stable covalent bonds
Trying to be a noble gas – like in the Lewis structure diagram showing electron pairs
Models 1:
Use stick and ball kits to make methane shown on slide CH4
Next make Ethane by adding C and 2 more H’s

3. Alkanes from Petroleum
methane ethane propane butane pentane
hexane octane decane
Made methane and ethane – make long chain hydrocarbons with fully saturated bonds
All alkanes
Series of names ‘mothers ever propagate babies’ M, E, P, B
Don’t need to know all the names
Models
Make butane from ethane
Look at how these move and can rotate about the single C bond. Can line up against each other.
Used as fuels. Long chains have higher boiling points, short chains are only gases at room temperature. “Saturated”
make butane (rotating bonds)

4. Structures and Formulae
Chemical (Molecular) formula
Structural formulae
Abbreviated structural formula
Structural Isomers, e.g. C6H14
Different ways of writing the same thing
Look at page 170 for explanation
Whiteboard:
Butane is
Chemical formula: C4H10
Structural formula- draw out H-C-C-C-C-H etc..
Abbv. structural formula:CH3-CH2-CH2-CH3
Can anyone think of another way to organise butane on your models?
Butane isomer: 2 methylpropane
Isomer activity: work in pairs
All isomers of C6H14
Large A 3 card each , set of small cards to place on the grid.
Answer sheets to give out when complete
Look for the longest chain with your finger
Look for the position of the branching to get the number

5. Functional Groups
Hydrocarbons are fairly dull, they burn and that’s about it….
Make them more interesting by altering the electronic structure and content
Use double bonds or add atoms such as O, N or Cl
Examples…
C=C double bonds
Alcohols
Carboxylic Acids
Esters
Amines
Amides
Haloalkanes
Hydrocarbons are not very reactive – they don’t ‘do’ much apart from burn (petrol, oil etc)
Molecules only react if by doing so they can become more stable, decrease in energy
Spice things up with other atoms or changing the electronic structure
Models
Back to ethane
How else can carbon bond? To itself
So turn ethane into ethene with a double bond C-C
Look at how this moves – it is rigid in the middle

6. Functional Groups
In the models we are using we have some standard atom colours to help us identify them…
Gong to look in more detail now at these functional groups – using a different kit
Molymod kit
Hand out with example ethanol and carboxylic acid

7. C=C bonds in Alkenes Double bonds are not free to rotate.
But they are reactive
Chemical feedstock
Cracking! page 187
make one
Added value…….
ETHENE
Molymod kit:
Make ethene using purple double bonds
Reactive feedstock for cracking
See next slide for adding water

8. Addition Reactions
Double bonds are very reactive Hydrogen (H2) can be added in.
Other things such as Bromine (Br2) can also be added.
Can add bromine – what colour is bromine?
Orange – standard test for the presence of double bonds – bubble through bromine and goes from orange to clear

9. Alcohols Add water – get an alcohol ETHANOL CH3CH2OH ETHANE 1,2 DIOL
HOCH2CH2OH
New naming system is descriptive
? Other names? Functions?
Add water to ethene and make alcohol – turning water into wine 
Ethanol is the one we drink
Molymod kit
Make ethanol – hair of the dog
Antifreeze is ethylene glycol – ethan 1,2 diol

10. Carboxylic Acids
By further oxidising alcohols we can make organic acids .
ethanoic acid CH3COOH
Oxidising means adding oxygen
Can make a weak acid – ethanoic acid
‘Oic’ – acid
Any other names for this?
Acetic acid – vinegar – on your chips
Methanoic acid? Other names?
Ant bite/ nettle sting – formic acid
Molymod kit
1. Make ethanoic acid
old name for ethanoic acid?
What about methanoic acid?

11. Condensation reactions
Lets do it
Make a model of ethanol and a model of ethanoic acid
THE reaction for producing the biopolymers we eat and are made of!
Condensation reaction is the most important chemical reaction for life
Condensation – the removal of water - just like condensation on your windows is the collection of water
The process of making proteins, fats or sugars are all condensation reactions
Models:
1. Take the ethanoic acid and the ethanol and condense them together
Makes ester (next slide) + water

12. Esters Ethyl ethanoate CH3COOCH2CH3 What is this ester used for?
Esters are ‘linking’ groups.
Small esters all have interesting smells.
Lovely linking lady with a beautiful perfume
Just add water

13. Hydrolysis the reverse of condensation The basis of digestion
Just add water
Hydrolysis
the reverse of condensation
The basis of digestion
Models:
1. Now reverse what you have just done – breaking big molecules down into smaller ones

14. Amines dimethylamine, CH3NHCH3
Amines contain nitrogen atoms. They are derived from ammonia, NH3.
Another important condensation reaction:
Like alcohols, amine groups will react with ethanoic acid, to produce......
Other functional groups include the amines:
Again can react with ethanoic acid to produce (next slide)

15. Amides
Amides are ‘linking’ groups. They exist in lots of forms and have lots of uses. Proteins are made from these amide linkages. More of this later..
N-ethylethanamide
CH3CONHCH2CH3
Looks like ester but has N in the middle of the chain
Lots of this in book 5 – proteins…

16. Functional Groups Examples… C=C double bonds Alcohols Carboxylic Acids
Esters
Amines
Amides
Haloalkanes
Recognition activity
Molymod kit exercise with sheet
pre-made examples with numbers
Match number to structural diagram on sheet
Circle the functional group in pencil on the sheet (TMA)

17. Getting familiar Turn over your notes –
how many functional groups can you remember between you?
Names only required!
C=C double bonds
Alcohols
Carboxylic Acids
Esters
Amines
Amides
Haloalkanes

18. Addition Polymers
Adding many ethene molecules together makes a polymer…
The real plastics have very long carbon chains >500 ethene units per molecule
polyethene
monomer repeating unit

19. Polyesters and Polyamides
Using ‘double ended’ molecules of acids with either alcohols or amines we can make condensation polymers.
Polyesters – use ‘ioic acids’
HOOC-CH2-COOH + HO-CH2-CH2-OH H2O is released in this ↓ condensation reaction.
HOOC-CH2-COO-CH2-CH2-OH + HOH The free COOH and OH groups can further react to make long chains
Polyester – what we are wearing
Ethanoic acid, esters

20. Amino acids The biological answer to condensation polymers.OH OH
CH3
CH2
CH2 O O O H H H N C C N C C N C C H H H OH OH OH H H H
Do the same with amino acids
Amine NH2 (amino) and ethanoic acid COOH (acid) at other end. R is standing for ‘something else added on here’
Single template is the basis for all proteins
Condensation can join amino acids together to make polymers – polypeptides – proteins
Rotation about C-C moves functional groups around
Simplest has just H at R – glycine
Some examples in the bag
Write out the condensation reaction between alanine and serine
Amide linkage plus water N in the chain
Alanine Phenylalanine Serine
Write down the condensation reaction* between alanine and serine, build the model as well.
Why are amino acids so efficient at polymerization ?

21. Proteins
Proteins are made from long chains of amino acids joined via peptide bonds. (polypeptides)
The 3D shape of proteins is vital to ensure that they function correctly in cells.
Come back to this again in book 5 – biopolymers
Inter molecular forces due to chemical structure having slight overall charge
What other inter molecular forces have you come across?
Types of forces on next slide
hydrogen “bonds”
van der Walls forces
ionic interactions (page 246)
hydrophobic interaction

22. Intermolecular forces
hydrogen “bonds”
van der Walls forces
ionic interactions
hydrophobic interaction

23. cis and trans
cis double bonds have the two hydrogen atoms on the same side
trans double bonds have the two hydrogen atoms on opposite sides
Cis and trans
Show examples in molymod kit
Trans – across trans pennine, cross dressing
Cis – same
Makes a difference to the functionality
This is in the TMA

24. Draw me: a fatty acid that contains 12 carbon atoms.
Counting the carbon of the carboxylic acid group as carbon 1, there is a cis carbon-carbon double bond between carbons 5 and 6 of the chain.
You should assume that, unless otherwise stated, all the carbon atoms are attached to other carbon atoms by single covalent bonds and there are sufficient hydrogen atoms to satisfy the valency of each carbon atom.
Activity as on the slide (TMA question)