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S104 Tutorial 4 Organic Chemistry
 

S104 Tutorial 4 Organic Chemistry

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Dr Jo Badge, R05, S104 Tutorial on Organic Chemistry

Dr Jo Badge, R05, S104 Tutorial on Organic Chemistry

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  • 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 CH 4 Next make Ethane by adding C and 2 more H’s
  • 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.
  • Different ways of writing the same thing Look at page 170 for explanation Whiteboard: Butane is Chemical formula: C 4 H 10 Structural formula- draw out H-C-C-C-C-H etc.. Abbv. structural formula:CH 3 -CH 2 -CH 2 -CH 3 Can anyone think of another way to organise butane on your models? Butane isomer: 2 methylpropane Isomer activity: work in pairs All isomers of C 6 H 14 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
  • 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
  • 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
  • Molymod kit: Make ethene using purple double bonds Reactive feedstock for cracking See next slide for adding water
  • 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
  • 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
  • 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
  • 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
  • Lovely linking lady with a beautiful perfume
  • Models: 1. Now reverse what you have just done – breaking big molecules down into smaller ones
  • Other functional groups include the amines: Again can react with ethanoic acid to produce (next slide)
  • Looks like ester but has N in the middle of the chain Lots of this in book 5 – proteins…
  • 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)
  • C=C double bonds Alcohols Carboxylic Acids Esters Amines Amides Haloalkanes
  • polyethene
  • Polyester – what we are wearing Ethanoic acid, esters
  • Do the same with amino acids Amine NH 2 (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
  • Sometimes it a for the same ting over and over – long chain hydrocarbon CH CH CH CH add infinitum Other times like in amino acid template, it means ‘another part of the molecule anything from H to benzene ring
  • 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
  • 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
  • Activity as on the slide (TMA question)

S104 Tutorial 4 Organic Chemistry S104 Tutorial 4 Organic Chemistry Presentation Transcript

  • CARBON RULES OK
    • S104 15 Jan 2010
    • agh/mcr/jb
    Organic Chemistry
  • Why Carbon ?
    • Group IV
    • 4 stable covalent bonds
    • Readily forms long chain structures such as those in fats and oil.
    • make ethane
  • 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)
  • Structures and Formulae
    • Chemical (Molecular) formula
    • Structural formulae
    • Abbreviated structural formula
    • Structural Isomers, e.g. C 6 H 14
    • page 170
  • 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
  • Functional Groups In the models we are using we have some standard atom colours to help us identify them…
  • 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
  • Addition Reactions Double bonds are very reactive. Hydrogen (H 2 ) can be added in. Other things such as Bromine (Br 2 ) can also be added .
  • Alcohols Add water – get an alcohol ETHANOL CH 3 CH 2 OH
    • ETHANE 1,2 DIOL
    • HOCH 2 CH 2 OH
    • New n aming system is descriptive
    • ? Other names? Functions?
  • Carboxylic Acids By further oxidising alcohols we can make organic acids . old name for ethanoic acid? What about methanoic acid? Pg 205 ethanoic acid CH 3 COOH
  • Condensation reactions
    • Lets do it
    • Make a model of ethanol and a model of ethanoic acid
    • Page 202
    • THE reaction for producing the biopolymers we eat and are made of!
  • Esters What is this ester used for? page 199 Ethyl ethanoate CH 3 COOCH 2 CH 3 Esters are ‘linking’ groups. Small esters all have interesting smells. ..........Just add water
  • Just add water Hydrolysis the reverse of condensation The basis of digestion
  • Amines Am ines contain nitrogen atoms. They are derived from am monia, NH 3 . Another important condensation reaction: Like alcohols, amine groups will react with ethanoic acid, to produce...... dimethylamine, CH 3 NHCH 3
  • 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 CH 3 CONHCH 2 CH 3
  • Functional Groups Examples… C=C double bonds Alcohols Carboxylic Acids Esters Amines Amides Haloalkanes
  • Getting familiar
    • Turn over your notes –
    • how many functional groups can you remember between you?
    • Names only required!
  • Addition Polymers Adding many ethene molecules together makes a polymer… The real plastics have very long carbon chains >500 ethene units per molecule monomer repeating unit
  • Polyesters and Polyamides Using ‘double ended’ molecules of acids with either alcohols or amines we can make condensation polymers. Polyesters – use ‘ioic acids’ HOOC-CH 2 -COOH + HO-CH2-CH2-OH H 2 O is released in this ↓ condensation reaction. HOOC-CH2-CO O-CH2-CH2-OH + H OH The free COOH and OH groups can further react to make long chains
  • Amino acids The biological answer to condensation polymers. O OH R C C O OH N H H H CH 3 C C O OH N H H H CH 2 C C O OH N H H H CH 2 OH Alanine Phenylalanine Serine Write down the condensation reaction* between alanine and serine, build the model as well. *Follow the pattern of 15.11 on page 225 Why are amino acids so efficient at polymerization ? C C N H H H
    • Memo about R
    • Page 202, 14.4
    • Page 221, 15.5
  • 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.
  • Intermolecular forces
    • hydrogen “bonds”
    • van der Walls forces
    • ionic interactions (page 246)
    • hydrophobic interaction
  • 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
    • see page 220
  • 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.