Organic Chemistry

Petroleum

  • Petroleum is a mixture of hundreds of different organic compounds.
  • It is used as fuel for cars, planes, trucks and ships. It is also burned for heat in factories, power stations, and homes.
  • It’s a non-renewable resource as we are using it up faster than it can form.

Refining Petroleum

  • To refine petroleum is to separate the compounds in it into groups with molecules of a similar size.
  • Petroleum is, by itself, not very useful. So, it has to be separated into fractions.
  • This is carried out by fractional distillation.
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  • These are the fractions collected after distilling petroleum:
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  • The larger the molecules in a hydrocarbon:
    1. The higher its boiling point
    2. The less volatile it is
    3. The more viscous it is
    4. The less flammable it is

Cracking

  • Cracking breaks down molecules into smaller ones.
  • You’d want to crack petroleum to get rid of impurities in it like sulphur, which can form harmful sulphur dioxide if left in the fuels.
  • In the lab, the long-chain hydrocarbon is heated in the presence of aluminium oxide as a catalyst. This causes it to undergo thermal decomposition.
  • In the refinery, the long-chain hydrocarbon is heated and vaporised. It is then passed over beds of hot catalyst. It then undergoes thermal decomposition.
  • Due to their double bond, the short-chain products of cracking are more reactive. So, they are used to make plastics and other substances.
  • It releases hydrogen:
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  • Decane just got crack’d
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Homologous series and Functional groups

  • In a homologous series:
    • All the compounds fit the same general formula.
    • The chain length increases by one each time.
    • As the chain gets longer, the compounds show a gradual change in their properties.
  • A functional group is the part of a molecule that largely dictates how that molecule will react.

Alkanes

  • Their general formula is C[n]H[2n+2]
  • They are saturated, ie. they contain only carbon - carbon single bonds.
  • The first four are gases at room temperature, while the next twelve are liquids. The rest are solids.
  • They are relatively less reactive because of stronger C-C and C-H bonds.
  • You really should know this, but their IUPAC suffix is ‘-ane’.
  • They undergo complete combustion in good supply of oxygen: CH4(g)+2O2(g)CO2(g)+2H2O(l)+heat energyCH_4 (g) + 2O_2 (g) \rightarrow CO_2 (g) + 2H_2O(l) + \text{heat energy}
  • If there is insufficient oxygen, they undergo incomplete combustion: 2CH4(g)+3O2(g)2CO(g)+4H2O(l)+less heat energy2CH_4 (g) + 3O_2 (g) \rightarrow 2CO(g) + 4H_2O(l) + \text{less heat energy}

Alkenes

  • General formula is C[n]H[2n]
  • They contain the C=C bond. This is their functional group.
  • They have the suffix ‘-ene’. Who knew?
  • They’re unsaturated because all their carbon-carbon bonds are not single.
  • It’s possible to make alkenes by cracking alkanes.
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Alkyl Groups

  • If you take away one hydrogen from an alkane, you’re left with an alkyl group. For instance:

    • This is methane
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    • But this is a methyl group
      Screenshot 2018-11-07 at 11 27 56 AM

  • This will be really useful when naming branched isomers, as well as other types of organic compounds.

  • It’s a surprise tool that’ll help us later.

Isomers

Isomers are compounds with the same formula, but different structures.

Alcohols

  • They have the functional group -OH (-O-H).
  • General formula is C[n]H[2n+1][OH]
  • Their suffix is ‘-anol’.

Ethanol

  • The Ethan(ol) Hunt is currently going on globally, as ethanol is really useful:
    • It is the alcohol in alcoholic drinks.
    • It is a good solvent. It dissolves many substances that do not dissolve in water.
    • It evaporates easily - it is volatile. This makes it a good solvent to use in glues, inks, perfumes and aftershave.
  • There are primarily two ways ethanol is made:
    • The biological way, fermentation:
      • This is made by breaking down glucose using the enzymes in yeast as a catalyst. This gives ethanol, carbon dioxide, and energy.

      • It is exothermic.
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      • All of the glucose isn’t converted to ethanol, because the yeast stops working as soon as the mixture gets too warm or when there is a certain percentage of ethanol produced.

      • So, it is separated from the mixture by fractional distillation.

Alkynes

  • Know about this only briefly
  • They have a carbon-carbon triple bond.
  • Their general formula is C[n]H[2n-2]
  • Their suffix is ‘-yne’.

Carboxylic acids

  • Functional group: -COOH
  • General formula: C[n]H[2n+1]COOH
  • It can be written as R-COOH where R represents an alkyl group.
  • Their suffix is ‘-anoic acid’.

Esters

  • Their general formula is R1-COO-R2, where R1 and R2 are two alkyl groups.
  • They are formed by reacting carboxylic acids with alcohols.
  • R1 comes from the carboxylic arid, where R2 comes from the alcohol.
  • This reaction is called a condensation reaction, because a water molecule is formed as a product.
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