Alkene structure and the C=C double bond (spec 4.22, 4.23, 4.24)
CₙH₂ₙ. One C=C. Ethene, propene, butene. sp² planar around C=C.
Alkenes are UNSATURATED HYDROCARBONS containing ONE C=C double bond per molecule.
General formula: (where n ≥ 2 — at least 2 carbons are needed for the double bond).
This is 2 fewer H atoms per molecule than the corresponding alkane (which is CₙH₂ₙ₊₂). The 'missing' 2 H atoms are because the C=C double bond uses up 2 H atoms' worth of bonding capacity.
First three alkenes.
| n | Name | Molecular formula | Structure |
|---|---|---|---|
| 2 | Ethene | C₂H₄ | CH₂=CH₂ |
| 3 | Propene | C₃H₆ | CH₂=CHCH₃ |
| 4 | Butene | C₄H₈ | CH₂=CHCH₂CH₃ (but-1-ene) or CH₃CH=CHCH₃ (but-2-ene) |
NO 'methene' — you need at least 2 carbons for the C=C. The smallest alkene is ETHENE (n = 2).
Displayed structural formula of ethene.
H H
\ /
C == C
/ \
H H
Ethene is a PLANAR molecule (all 6 atoms in the same plane). The two carbons share TWO bonds (a double bond):
- One σ bond (head-on overlap of orbitals — the same type as in alkanes).
- One π bond (sideways overlap above and below the molecular plane — only in double/triple bonds).
Each carbon is sp² hybridised: 3 single bonds in a flat trigonal arrangement, with the π bond perpendicular. Bond angle ~ 120° (NOT 109.5° as in alkanes).
Bond strengths.
| Bond | Energy (kJ/mol) |
|---|---|
| C–C single bond | 348 |
| C=C double bond (total: σ + π) | 612 |
| C=C π bond alone | ~ 264 |
The π bond is significantly WEAKER than the σ bond — it can be broken (during addition reactions) while leaving the σ bond intact.
Positional isomerism in butene.
For C₄H₈, the double bond can be in different positions:
- But-1-ene: C=C between C1 and C2. CH₂=CHCH₂CH₃.
- But-2-ene: C=C between C2 and C3. CH₃CH=CHCH₃.
These are POSITIONAL isomers — same molecular formula, different position of the C=C. Different compounds with slightly different boiling points and chemical behaviour.
(Plus cyclobutane and methylenecyclopropane — also C₄H₈ but in ring forms, not relevant to 4CH1.)
Why alkenes are MORE REACTIVE than alkanes.
Three reasons related to the C=C double bond:
-
The π bond is WEAKER than a single bond (~ 264 vs ~ 348 kJ/mol). Easier to break.
-
The π bond is EXPOSED — the electron density of the π bond sticks out above and below the plane of the molecule (unlike σ bonds, which are inside the bond axis). Reagents can approach and attack the π electrons directly.
-
The π bond is ELECTRON-RICH — high electron density between the two carbons. This makes it electron-donating ('nucleophilic' towards an electrophile). Electrophiles like Br₂ are attracted to the C=C and react with it.
In contrast, alkanes have only single C–C and C–H bonds → no exposed electron-rich region → no easy target for reagents → unreactive at room T.
The 'extra' bond in alkenes is what makes them undergo a whole class of reactions (additions) that alkanes cannot.
Industrial origin.
Alkenes are NOT naturally present in crude oil — the C=C bond is too reactive to survive geological time. Alkenes are produced INDUSTRIALLY by CRACKING long-chain alkanes (see Topic 4.2 — Crude Oil):
- Catalytic cracking: long alkane → shorter alkane + alkene.
- Example: C₁₀H₂₂ → C₈H₁₈ + C₂H₄.
So ethene (C₂H₄) — the most-produced organic chemical in the world (~ 150 million tonnes/year) — comes from cracking.
Uses of alkenes — the plastics industry.
Alkenes are the MONOMERS for most common plastics:
- Ethene → polyethene (poly(ethene), polythene) — bags, bottles, films.
- Propene → polypropene — containers, fibres, car parts.
- Styrene (an alkene with a benzene ring) → polystyrene.
- Chloroethene (vinyl chloride) → PVC.
Without alkenes (and the cracking that makes them), there would be no plastics industry.
- Alkenes: unsaturated, general formula CₙH₂ₙ (n ≥ 2).
- First three: ethene C₂H₄, propene C₃H₆, butene C₄H₈.
- One C=C double bond per molecule (σ + π).
- sp² carbons, planar around C=C, bond angle ~120°.
- MORE REACTIVE than alkanes: π bond weaker + exposed + electron-rich.
- Made by cracking long alkanes from crude oil; not naturally in oil.
- Used to make plastics (polyethene, polypropene).
- Positional isomers possible from butene onwards (but-1-ene vs but-2-ene).