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Flashcards · 7405 · AS Topic 23

Alcohols (AS Level) flashcards

16 cards on AS Topic 23, subtopics 3.3.5.1 to 3.3.5.3. Pick a subtopic or study them all.

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3.3.5.1 Alcohol production

Hydration of ethene: equation and conditions
CH₂=CH₂ + H₂O → CH₃CH₂OH. Steam, about 300 °C, high pressure, acid catalyst such as phosphoric acid on a solid support.
Fermentation of glucose: equation and conditions
C₆H₁₂O₆ → 2C₂H₅OH + 2CO₂. Yeast enzymes, around 35 °C, anaerobic, aqueous.
Fermentation temperature
Too cold → slow; too hot → yeast enzymes denature. About 35 °C is a compromise.
Why must fermentation be done without air?
Oxygen would oxidise ethanol to ethanoic acid, and yeast would respire aerobically to CO₂ and water.
Why is bioethanol only "carbon neutral" on paper?
6 CO₂ are absorbed in photosynthesis and 6 released by fermentation (2) and combustion (4). But fossil fuels used for farm machinery, fertiliser, distillation and transport release more CO₂.

3.3.5.2 Oxidation of alcohols

Primary, secondary and tertiary alcohols
The carbon bonded to –OH is bonded to one, two or three other carbons respectively (methanol counts as primary).
Oxidising agent for alcohols and its colour change
Acidified potassium dichromate(VI), K₂Cr₂O₇ / H₂SO₄: orange → green (Cr₂O₇²⁻ → Cr³⁺).
Primary alcohol: how do you get the aldehyde rather than the carboxylic acid?
Aldehyde: distil it off as it forms (it has no hydrogen bonding, so it boils lowest). Carboxylic acid: heat under reflux with excess dichromate.
Products of oxidising a secondary and a tertiary alcohol
Secondary: a ketone. Tertiary: no reaction (stays orange), because there is no H on the carbon bonded to –OH.
Equation for the oxidation of propan-1-ol to propanal
CH₃CH₂CH₂OH + [O] → CH₃CH₂CHO + H₂O
Tollens’ and Fehling’s results with an aldehyde
Tollens’: silver mirror. Fehling’s: blue → red precipitate. A ketone gives no change with either. Warm in a water bath.

3.3.5.3 Elimination

Dehydration of an alcohol: reagent and conditions
Heat with concentrated sulfuric acid or concentrated phosphoric acid. An alkene and water form.
Outline the three stages of the mechanism for alcohol elimination
A lone pair on O takes H⁺, forming R–OH₂⁺; the C–O bond breaks and H₂O leaves, giving a carbocation; electrons from an adjacent C–H bond form C=C and H⁺ is released.
Which alkenes form when 2-methylbutan-2-ol is dehydrated?
2-methylbut-1-ene and 2-methylbut-2-ene. Neither shows E–Z isomerism.
Why is making ethene from ethanol useful?
Ethanol from fermentation → ethene → poly(ethene), so addition polymers can be made without crude oil.
Required practical 5: purifying cyclohexene from the crude distillate
Shake with sodium carbonate solution in a separating funnel (release CO₂), discard the aqueous layer, wash with water, dry with anhydrous CaCl₂ or MgSO₄, then redistil.