Alcohols, Carboxylic Acids and Esters
Ethanol is made by fermentation (yeast + sugar, 25–35 °C, no air; renewable but slow and impure) or hydration of ethene (steam, 300 °C, 60 atm, phosphoric acid; fast and pure but from non-renewable oil). Ethanol burns cleanly and is a solvent and fuel. Oxidising ethanol gives ethanoic acid, a weak acid that reacts with metals, bases and carbonates. An acid + an alcohol (with conc. catalyst) gives an ester, e.g. ethyl ethanoate, used in perfumes and flavourings.
Learning objectives
- Compare fermentation and hydration for making ethanol.
- Describe the combustion and oxidation of ethanol.
- Describe reactions of carboxylic acids.
- Name esters and write esterification equations.
Brazil runs many of its cars on ethanol made from sugar cane, while the UK makes ethanol for industry from ethene. Why the different choices?
Core idea
Leave grape juice with yeast and it becomes wine (ethanol). Leave the wine open to the air and bacteria turn it sour: vinegar (ethanoic acid). Two organic families, one after the other.
Ethanol is made by fermentation or by hydrating ethene. Oxidising ethanol gives ethanoic acid. Acids and alcohols together make esters.
1. Two ways to make ethanol
Renewable but slow, or fast but from oil.
2. Esters
Ethanoic acid reacts with methanol.
- Goal
- Equation and ester name.
- Strategy
- Acid + alcohol → ester + water.
- –OH from the acid and H from the alcohol form water.
- Alcohol part (methyl) first, acid part (ethanoate) second.
Why do fermented drinks rarely exceed about 15% ethanol?
Summary
- Fermentation vs hydration.
- Ethanol → ethanoic acid by oxidation.
- Acid + alcohol → ester + water.
- Fermentation
- Conversion of sugar to ethanol and CO₂ by yeast.
- Ester
- Compound formed from a carboxylic acid and an alcohol.
- Hydration
- Adding water (steam) to a molecule.
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