Organic Chemistry
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Organic Chemistry

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A set of slides created to teach Organic Chemistry to learners at Bishops Diocesan College in Cape Town.

A set of slides created to teach Organic Chemistry to learners at Bishops Diocesan College in Cape Town.

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  • 1. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net ORGANIC CHEMISTRY K Warne
  • 2. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Distillation of Crude Oil
  • 3. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Homologous series This is a series of compounds which all contain the same functional group, and have similar chemical properties. ALKANES ALKENES ALCOHOLS CH4 CH2 =CH2 CH3OH CH3-CH3 CH2 =CH –CH3 CH3CH2OH CH3-CH2-CH3 CH2 =CH – CH2 – CH3 Each has a general formula: ALKANES: CnH2n+2 ALKENES: CnH2n ALCOHOLS: CnH2n+1OH The members of the series differ by the number of CH2 units. CH3-CH3, CH3-CH2-CH3, CH3 -CH2 -CH2 -CH3 Graduation in physical properties: eg: boiling points. CH4 (GAS), C8 H18 (LIQUID), C30 H62 (SOLID) As chains get longer Melting points increase (London forces get stronger) as molecule surface area increases.
  • 4. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net C C C C C C C C H H H H H H H H H H H H H H H H H H 3-ethylhexane
  • 5. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Examples of Alkenes ETHENE, C2H4 H H C C H H OR CH2 CH2 PROPENE CH2 CH CH3 TASK: Use ball & stick models or sketches to construct and name 3 different structures for C4H8 each one with one double bond. CH3CH2CH CH2 CH3CH CHCH3 CH3C CH2 CH3 BUT-1-ENE BUT-2-ENE METHYL PROPENE H H C C H CH3
  • 6. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Functional groups The functional groups are ………………. or ………………….. of atoms which determine the ……………………. of organic molecules.
  • 7. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net STRUCTURES OF ALKANES METHANE ………. Bond Angle ……………. Shape ……………………… Can be illustrated as:
  • 8. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net THE RULES FOR NAMING ORGANIC COMPOUNDS 1. Choose the longest unbroken chain of Carbon atoms and assign a name for the carbon chain using the prefixes; meth-1, eth-2 etc. 2. Identify any carbon chain branches (alkyl groups). These are assigned names using the same prefixes as above along with the suffix “-yl” – methyl, ethyl etc. 3. Identify the functional groups present in the molecule. Assign a prefix or suffix according to their homologous series. These will be written in front of the name of the carbon chain. 4. There is an order of precedence, to decide the suffix for the carbon chain: COOH / C=C > OH > Br / Cl 5. Number the Carbon atoms in the longest chain so that the branches/functional groups have the lowest number possible. Allocate a number for every group/branch no matter how many times it occurs. Where groups are on the same carbon write their names in alphabetical order. 6. Numbering takes precedence "wins" over alphabetical spelling. Prefixes are used for groups that occur more than once. Di – 2 Tri – 3 Tetra – 4 Penta – 5 etc. 7. The final name is written as one word with commas between numbers, hyphens separating numbers from words.
  • 9. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net CH3–CH2–CH2–CH2Br PRIMARY 10 CH3–CH2–CH–CH3 Br SECONDARY 20……………………………. TERTIARY 30 ………………………………………………..CH3 CH2–C–CH3 CH3 Br ………………………….
  • 10. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net General formula ………………………………. •CH3OH ………………… •CH3CH2OH ……………… •C3H7OH – two isomers TASK: C4H9OH has 4 isomers. Draw the structures of each isomer giving the name and class of each one.
  • 11. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net KNOWN AS ................... STRUCTURE C O BOND ANGLE .............. ALDEHYDES GENERAL STRUCTURE R C O H EXAMPLES HCHO - ............................. CH3CHO - .................. CH3CH2CHO - ................  Illustrate the structures of these examples
  • 12. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net
  • 13. For FULL presentation click HERE >> www.warnescience.net Carboxylic Acids GENERAL FORMULA EXAMPLES HCOOH methanoic acid CH3COOH ethanoic acid CH3CH2COOH propanoic acid  Illustrate the structures of these examples. Name the anion formed in the acidic reaction. Acidic reaction CH3COOH + H2O  CH3COO- + H3O+ R C O OH Carboxyl group -COOH SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> ScienceCafe
  • 14. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net FORMATION OF ESTERS • GENERALLY: ACID + ALCOHOL ESTER + WATER catalysed by H+ ions normally from conc. H2SO4 O O R C + H O R/ R C + H2O OH O R/ O O H C + CH3OH H C + H2O OH O CH3 methanoic methanol methyl methanoate CH3CH2OH + CH3CH2COOH CH3CH2COOCH2CH3 + H2O
  • 15. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Physical Properties Recognize and apply to particular examples the relationship between melting points, boiling points, vapour pressure, viscosity and intermolecular forces (hydrogen bonding, Van der Waals forces including dispersion or London forces number and type of functional group, chain length, branched chains) PHYSICAL PROPERIES • vapour pressure • melting points • boiling points • viscosity BONDING & STRUCTURE • IMF • Chain Length • Branches • Functional groups (no & type)THESE DEPEND ON THESE!
  • 16. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net + - + - + - + - + - + - + - BONDING & STRUCTURE • Chain Length – long chains increase IMF CCCCCCC H H HH HH HH HH HH HH H H CCCCCCC H H HH HH HH HH HH HH H H Large surface area  stronger van der waals forces (IMF) CC C C C H H HH H H H H H H H H CC C C C H H HH H H H H H H H H Shorter or branched chains have less surface area .: weaker IMF • Branches – shorten chain – reduce IMF Lots of dipoles strong force! + - + - + - + - Fewer dipoles weak force!
  • 17. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Reaction Type Reaction NAME (Type of type) Applies to Forms Example Conditions/Notes ADDITION Halogenation Alkene/ynes Haloalkanes alkene + Br2  haloalkane X2 added to alkene Hydrohalegenation Alkene/ynes Haloalkanes alkene + HBr  haloalkane No Water present, H attatches to carbon with MOST H's Hydration Alkene/ynes Alcohols alkenes + H2O  alcohols XS H2O small amount of stron acid HX or H3PO4 H goes onto C with MOST H's hydrogenation Alkene/ynes Alkanes alkenes + H2 alkanes alkene in N-polar solvent (Pt, Pd or Ni cat - atmosphere of H2) SUBSTITUTION Halogenation Alkanes Haloalkanes CH4 + Cl2  CH3Cl + HCL u.v light cataktst Hydrolysis Haloalkanes Alcohols C2H5Br (EtOH) + NaOH(aq) +  C2H5OH + NaBr Ethanolic haloalkane, aq hydroxide, warm halogenation Alcohols Haloalkanes CH3OH + H2504 + NaBr  CH3Br + H2O primary & Secondary alcohols need c H2S04 + NaX, Tertiary room temp ELIMINATION Cracking Alkanes smaller alkanes + ethene heat and or catalyst Dehydration Alcohols alkenes Alcohol --> alkene + H2O H removed from C with least hydrogens (Gases heat Al2O3 cat) or liq cH2SO4 (or H3PO4) Dehydrohalogenatio n Haloalkanes ALkenes CH2Cℓ-CH2Cℓ → CH2 = CHCℓ + HCℓ Reflux, conc NaOH or KOH in ethanol (Hot ethanolic...) Esterification Alcohols & carboxylic acids Esters c acid + alcohol --> ester + H2O conc sulphuric acid + heat COMBUSTION COMBUSTION All CO2 + H20 CH 50H + 302 --> 2C02+3H20 XS O2 complete --> CO2; insufficient O2 --> CO
  • 18. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Addition reactions • Unsaturated compounds undergo addition reactions to form saturated compounds e.g. With any halogen (F2 Cl2 Br2 & I2) CH2=CH2 + Cℓ2  CH2Cℓ-CH2Cℓ With Br2 (aq) (brown liq) the decolourization is used as a test for alkenes • hydrohalogentaion - addition of HX - halogenation - addition of X2 – CH3CH=CH2 + HX  CH3CHXCH3 (no water present) • hydration - addition of H2O – CH3CH=CH2 + H2O  CH3CH OHCH3 (acid catalyst) (The X-atom or OH-group attaches to the more substituted C-atom.) • hydrogenation - addition of H2 CH3CH=CH2 + H2  CH3CH2CH3 (high temp Ni cat.) (Used in the hardening of oils to make margarine) (alkene dissolved in a non-polar solvent with catalyst (Pt, Pd or Ni) in an H2 atmosphere )
  • 19. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Elimination reactions • * Saturated compounds (haloalkanes, alcohols, alkanes) undergo elimination reactions to form unsaturated compounds e.g. CH2CℓCH2Cℓ  CH2=CHCℓ + HCℓ • - dehydrohalogentaion - elimination of HX from a haloalkane (alkene with the more highly substituted double bond is the major product). – CH3CH2CH2 X  (hot ) • dehydration - elimination of H2O from an alcohol (alkene with the more highly substituted double bond is the major product). – CH3CH2CH2 OH  ( conc ) • dehydrogenation - elimination of H2 from an alkane. -. CH3CH2CH3  • cracking of alkanes C16 H34  C9H20 + + 2 CH2=CH2 ( )
  • 20. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Substitution reactions Reactions of HX with alcohols e.g. ALCOHOL + HX  HALOALKANE + WATER (CH3)3OH + HBr → • Reactions where the OH of alcohols are substituted with a halogen e.g. HALOALKANE + KOH  (CH3)3Br + KOH → • Two types of saturated structure can be inter-converted by substitution as shown in the above two reaction equations. ALCOHOL  HALOALKANE  • * Reactions of X2 with alkanes in the presence of light (prior knowledge from Grade 11). • Cl2 + CH4 
  • 21. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Substitution Conditions • Tertiary alcohols: HBr or HCl room temp • Primary & Secondary: cH2SO4 solid NaBr/KBr cH2SO4 + NaBr(s)  HBr (+ Na2SO4) Treat primary and secondary alcohols with concentrated H2SO4 and solid NaBr (or KBr). The H2SO4 and solid NaBr react to form HBr: H2SO4 + NaBr → HBr + NaHSO4 The HBr reacts with the alcohol to form the bromoalkane: e.g. CH3CH2OH + HBr → CH3CH2Br + H2O SAMPLE ONLY SAMPLE ONLY
  • 22. SAMPLE ONLY SAMPLE ONLY SAMPLE ONLY For FULL presentation click HERE >> www.warnescience.net Hi… This is a SAMPLE presentation only. My FULL presentations, which contain a lot more slides and other resources, are freely available on my resource sharing website: www.warnescience.net (paste into your browser if link above does not work) Have a look and enjoy! Keith Warne WarneScience