Alcohol structure and the –OH functional group (spec 4.27, 4.28)
CₙH₂ₙ₊₁OH. Methanol, ethanol, propan-1-ol. Soluble in water (–OH H-bonds).
Alcohols are a homologous series of organic compounds characterised by the HYDROXYL group –OH bonded to a carbon atom.
General formula: .
This represents an alkyl group (CₙH₂ₙ₊₁ from the corresponding alkane) with one H replaced by an OH group.
First three alcohols.
| n | Name | Structural formula | Molecular formula | bp (°C) |
|---|---|---|---|---|
| 1 | Methanol | CH₃OH | CH₄O | 65 |
| 2 | Ethanol | CH₃CH₂OH (or C₂H₅OH) | C₂H₆O | 78 |
| 3 | Propan-1-ol | CH₃CH₂CH₂OH | C₃H₈O | 97 |
Naming pattern. Take the alkane name (methane, ethane, propane) → drop the '-e' → add '-ol'. For 3+ carbons, include a LOCANT (number) indicating which carbon carries the –OH: propan-1-ol (OH on C1) vs propan-2-ol (OH on C2, the middle carbon).
Positional isomerism — propan-1-ol vs propan-2-ol.
Both have the same molecular formula C₃H₈O but different positions of the –OH group:
| Property | Propan-1-ol | Propan-2-ol |
|---|---|---|
| Structural formula | CH₃CH₂CH₂OH | (CH₃)₂CHOH or CH₃CH(OH)CH₃ |
| –OH position | C1 (end carbon) | C2 (middle carbon) |
| Boiling point | 97 °C | 82 °C |
| Smell | Sharp, alcoholic | Slightly sweet |
Both are alcohols, both have the –OH functional group, both share most of the same chemistry — they just differ slightly in physical properties because of the different molecular shape.
Displayed formula of ethanol.
H H
| |
H-C-C-O-H
| |
H H
The –OH group is at the end. Ethanol has 2 C, 6 H, 1 O = C₂H₆O.
Why short-chain alcohols are LIQUIDS at room temperature.
Compare with the corresponding alkanes:
| Alcohol | bp (°C) | Alkane | bp (°C) |
|---|---|---|---|
| Methanol | 65 | Methane | –162 |
| Ethanol | 78 | Ethane | –89 |
| Propan-1-ol | 97 | Propane | –42 |
Each alcohol has a MUCH HIGHER bp than the corresponding alkane (despite similar molecular masses). Why?
HYDROGEN BONDING. The –OH group of alcohols is polar (O is much more electronegative than H, so the O has a δ⁻ charge and the H has a δ⁺ charge). The δ⁻ O of one molecule attracts the δ⁺ H of another molecule → forms a hydrogen bond. Hydrogen bonds are much stronger than the van der Waals forces between alkane molecules → much more energy required to separate alcohol molecules → much higher boiling points.
Alkane molecules have only weak van der Waals forces (no polar groups) → much lower bp.
Why short-chain alcohols are SOLUBLE in water.
Water (H₂O) is also a polar molecule that forms hydrogen bonds. Alcohols can hydrogen-bond DIRECTLY with water (alcohol's –O-H to water's O, or vice versa) → the alcohol molecules disperse easily into water → high solubility.
| Alcohol | Solubility in water |
|---|---|
| Methanol | Fully miscible (any ratio) |
| Ethanol | Fully miscible |
| Propan-1-ol | Fully miscible |
| Butan-1-ol | Partially soluble (~ 8 g/100 mL) |
| Pentan-1-ol | Slightly soluble (~ 2 g/100 mL) |
As the alkyl chain gets longer, the non-polar hydrocarbon part dominates → water solubility drops. Long-chain alcohols (C₁₀+) are essentially insoluble in water.
The dual nature of alcohols.
Alcohols have BOTH polar (–OH) and non-polar (alkyl chain) regions → they can dissolve in both water (via –OH H-bonding) AND non-polar solvents (via van der Waals on the alkyl part). This makes them excellent SOLVENTS that can dissolve a wide range of substances — useful for perfumes, cleaning agents, paint thinners, antiseptics.
Industrial production: methanol vs ethanol.
- Methanol: made on huge scale by catalytic conversion of synthesis gas (CO + 2H₂ → CH₃OH, Cu/ZnO/Al₂O₃ catalyst, 250 °C, 50-100 atm). Used as chemical feedstock for plastics + biodiesel.
- Ethanol: made by TWO routes — hydration of ethene (industrial petrochemical) and fermentation of glucose (biological, used for drinks + biofuel). Detail in the next section.
Common uses.
| Alcohol | Uses |
|---|---|
| Methanol | Industrial solvent, chemical feedstock, biodiesel production, antifreeze (windscreen washer). POISONOUS to humans. |
| Ethanol | Alcoholic drinks (beer ~5%, wine ~12%, spirits ~40%); solvent (perfumes, paints, mouthwash); biofuel; antiseptic / hand sanitiser; chemical feedstock. |
| Propan-1-ol & propan-2-ol | Solvents, antiseptics, screen cleaners, automotive products. |
Safety: methanol is POISONOUS.
NEVER drink methanol. In the body, methanol is metabolised in the liver to METHANAL (HCHO) and METHANOIC ACID (HCOOH), which damage:
- The optic nerve → causes BLINDNESS (just 10 mL can cause permanent damage).
- Metabolic acidosis → coma and death (30 mL can be fatal).
This is why methanol is added to industrial ethanol to make 'methylated spirits' (denatured alcohol) — undrinkable but tax-free for industrial use.
- Alcohols: CₙH₂ₙ₊₁OH, –OH functional group.
- Methanol CH₃OH, ethanol CH₃CH₂OH, propan-1-ol CH₃CH₂CH₂OH.
- Liquids at room T, soluble in water (hydrogen bonding with H₂O).
- Higher bp than corresponding alkanes — H-bonding between alcohol molecules.
- Positional isomerism: propan-1-ol vs propan-2-ol (same molecular formula, different OH position).
- Methanol POISONOUS (causes blindness and death — methylated spirits).
- Ethanol = drinks, solvent, fuel, sanitiser. Methanol = industrial solvent + feedstock.