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Making alcohol: Fermentation
- catalysed by an enzyme in yeast (zymase)
- 37C
- anaerobic
- concentration of 14% alcohol by volume
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Making alcohol: Hydration of ethene
- catalyst: phosphoric acid
- high temperature: 300C
- 60 atm
- uses steam
- 95% conversion
- unreacted gases are recycled and passed through the reactor again
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Uses of alcohols
- Methanol: clean burning fuel, feedstock, can be converted into methanal and ethanoic acid
- Ethanol: drink, perfumes, cleaning fluids, fuel
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Properties of alcohols
- Water solubility: hydrogen bonds form between the polar -OH groups of alcohol and water molecules
- Volatility and boiling points: high melting and boiling points, low volatility because of hydrogen bonds
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Primary alcohol
- -OH group attached to C bonded to no or one alkyl group
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Secondary alcohol
- -OH group attached to a C bonded to two alkyl groups
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Tertiary alcohol
- -OH group is attached to a C bonded to three alkyl groups
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Combustion of alcohols
- Alcohols burn completely to form carbon dioxide and water
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Oxidation of primary alcohols
- Distil: form an aldehyde, catalyst is acidified potassium dichromate solution (K2Cr2O7/H2SO4)
- Reflux: form a carboxylic acid, same catalyst
- Solution turns from orange to green
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Oxidation of secondary alcohols
- Heat: form a ketone, catalyst is acidified potassium dichromate (K2Cr2O7/H2SO4)
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Oxidation of tertiary alcohols
- resistant to oxidation
- oxdidating agents remains orange
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Esterifaction of alcohols
- alcohol is warmed with a carboxylic acid
- acid catalyst: usually concentrated sulfuric acid
- an ester and water is produced
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Dehydration of an alcohol
- form an alkene
- heating under reflux
- phosphoric acid catalyst present
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Halogenoalkanes
- general formula: CnH2n+1X (X is the halogen)
- fluoro- F
- chloro- Cl
- bromo- Br
- iodo- I
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Uses of halogenoalkanes
- refridgerants
- aerosol propellants
- dry-cleaning solvents
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Halogenoalkanes- carbon-halogen bond
- Polar: halogen atoms are more electronegative than carbon atoms, bonded electron pair is attracted more towards the halogen atom
- polarity decreases down the halogen group- electronegativity decreases
- electron-deficient carbon atom attracts nucleophiles
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Nucleophile
electron pair donor
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Hydrolysis of halogenoalkanes
a nucleophilic substitution reaction: a nucleophile is attracted to an electron-deficient centre or atom where it donates a pair of electrons to form a new covalent bond
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Hydrolysis of a primary halogenoalkane
- reaction with hot aqueous acid
- the halogen atom is replaced by a hydroxide ion
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Rates of primary halogenoalkane hydrolysis
- Polarity: C-F bond is the most polar amongst the halogenoalkanes, so the carbon atom should attract the nucleophile most readily and give the fastest reaction...
- But...
- Bond enthalpy is more important the polarity
- Bond enthalpy: C-I bond is the weakest so is broken more easily, so has a faster reaction . As the rate of raction increases, the bond enthalpy weakens
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Experiment to show rate of hydrolysis
heating halogenoalkane with aqueous silver nitrate with ethanol added
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Chloroethene in the production of PVC
- Uses: drainpipes, plastic window frames, sports equipment, toys, packaging
- polymerisation of chloroethene
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Tetrafluoroethene in the production of PTFE
- Uses: coating pans, nail polish
- polymerisation of tetrafluoroethene
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CFC's
- They were first developed, because refrigeration gases at the time were toxic. CFC replaced these gases as it was non-toxic and unreactive.
- CFC's remain stable until they reach the stratosphere, where hey break down in the presence of UV radiation to form chlorine radicals. These radicals catalyse the breakdown of the ozone layer
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Percentage yield
- Yield can be moles or mass
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Atom economy
- Benefits of high atom economy: reduced amount of waste products
- Addition reactions: 100% atom economy, no waste products
- Substitution reactions: waste products, less efficient
- Some reactions have a high percentage yield but low atom economy
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Infrared spectroscopy
- absorption of infrared radiation causes covalent bond to vibrate (stretching or bending motion)
- breathalysers: measure ethnol levels by using infrared spectroscopy
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Mass spectrometry
- Early developments: used to determine the mass-to-charge ratios of ions
- Uses: to identify unknown compounds, to determine the abundance of each isotope in an element, to gain further information abou the structure and chemical properties of molecules
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Reaction mechanism: radical substitution
- UV radiation provides the energy to break the covalent bond
- Bonds break by homolytic fission
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Reaction mechanism: electrophilic addition
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Reaction mechanism: nucleophilic substitution
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