CARBON RULES OK

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CARBON RULES OK
Organic Chemistry

• SCH3U/4U/4C
• Mr. Bauernschmitt
• General Panet HS

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Why Carbon ?

• Group IV
• 4 stable covalent bonds
• Readily forms long chain structures such as those
  in fats and oil.
• make ethane

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Alkanes from Petroleum
methane ethane propane
butane pentane
hexane octane
decane
Used as fuels. Long chains have higher boiling
points, short chains are only gases at room
temperature. Saturated make butane
(rotating bonds)
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Structures and Formulae

• Chemical (Molecular) formula
• Structural formulae
• Abbreviated structural formula
• Structural Isomers, e.g. C6H14

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Functional Groups

• Hydrocarbons are fairly dull, they burn and
  thats 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 CC double bonds Alcohols Carboxylic
Acids Esters Amines Amides Haloalkanes
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Functional Groups
In the models we are using we have some standard
atom colours to help us identify them
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CC bonds in Alkenes
Double bonds are not free to rotate. But they
are reactive Chemical feedstock Cracking! page
187 make one Added
value.
ETHENE
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Addition Reactions
Double bonds are very reactive.
Hydrogen (H2) can be added in.
Other things such as Bromine (Br2) can also be
added.
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Alcohols
Add water get an alcohol
ETHANOL CH3CH2OH

• ETHANE 1,2 DIOL
• HOCH2CH2OH
• New naming system is descriptive
• ? Other names? Functions?

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Carboxylic Acids
By further oxidising alcohols we can make organic
acids .
ethanoic acid CH3COOH

old name for ethanoic acid? What about methanoic
acid?
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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!

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Esters
Ethyl ethanoate CH3COOCH2CH3
What is this ester used for?
Esters are linking groups. Small esters all
have interesting smells.
..........Just add water
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Just add water

• Hydrolysis
• the reverse of condensation
• The basis of digestion

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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......
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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
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Functional Groups
Examples CC double bonds Alcohols Carboxylic
Acids Esters Amines Amides Haloalkanes
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Getting familiar

• Turn over your notes
• how many functional groups can you remember
  between you?
• Names only required!

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Addition Polymers
Adding many ethene molecules together makes a
polymer
The real plastics have very long carbon chains
gt500 ethene units per molecule
monomer repeating unit
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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-O
H HOH The free COOH and OH
groups can further react to
make long chains
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Amino acids
The biological answer to condensation
polymers.
R
O
OH
OH
CH3
CH2
CH2
O
O
O
H
H
H
C
C
C
C
C
C
N
N
N
H
H
H
OH
OH
OH
H
H
H
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 ?
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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.
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Intermolecular forces

• hydrogen bonds
• van der Walls forces
• ionic interactions
• hydrophobic interaction

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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

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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.