854496
Description
Mind Map by Stephen Cole, updated more than 1 year ago
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Created by Stephen Cole
almost 10 years ago
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The formation and reactions of alcohols
- Formation from haloalkanes (nucleophilic
substitution)
- Favoured in aqueous conditions, just
above room temp, primary haloalkanes
- Lone pair on hydroxide ion attacks electron
deficient carbon, replacing halogen
- Reagents: haloalkane + hydroxide ion
- Favoured in aqueous conditions, just
above room temp, primary haloalkanes
- Dehydration
- Elimination to form an alkene
- Heated with excess sulfuric acid at 600K
- Vapours passed over molten aluminium oxide catalyst
- Elimination to form an alkene
- Oxidation
- Oxidising agent is orange acidified potassium dichromate(VI)
- Reduced to green chromium(III) ions
- Reduced to green chromium(III) ions
- Primary alcohol
- Aldehyde
- Carboxylic acid (excess oxidising
agent, reflux)
- Brick-red solid produced with
Fehlng's reagent
- Silver formed with Tollens' reagent
- Carboxylic acid (excess oxidising
agent, reflux)
- Aldehyde
- Secondary alcohol
- Ketone resistant to further oxidation
- No change when added to Fehling's or Tollen's
- No change when added to Fehling's or Tollen's
- Ketone resistant to further oxidation
- Tertiary alcohols resistant to oxidation
- Oxidising agent is orange acidified potassium dichromate(VI)
- Formation from ethene (hydration)
- Mechanism: electrophilic
addition
- Hydrogen on water attracted to electron-rich double bond
- Hydroxide ion attacks resulting carbocation
- Hydroxide ion attacks resulting carbocation
- Hydrogen on water attracted to electron-rich double bond
- 600K, 6.5mPa, concentrated phosphoric acid catalyst
- Temperature compromise between yield and ROR
- Pressure compromise between yield and cost
- Temperature compromise between yield and ROR
- Mechanism: electrophilic
addition
- Formation from glucose (fermentation)
- Yeast enzyme (zymase)
- Aqueous, anaerobic conditions, approx 37 degrees C
- Carbon dioxide produced
- Glucose comes from sugar beet or sugar cane
- Batch process
- Yeast enzyme (zymase)
- Hydration of ethene vs. fermentation
- Hydration of ethene
- 100% atom economy (ethanol only product)
- Doesn't use up land that could be used for food
- Continuous process rather than
batch
- Purer yield of ethanol
- 100% atom economy (ethanol only product)
- Fermentation of glucose
- Much lower temperature and pressure =
lower energy costs
- Carbon-neutral "bioethanol"
- Renewable source
- Doesn't involve cracking of hydrocarbons-
high cost process
- Much lower temperature and pressure =
lower energy costs
- Hydration of ethene
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