Lesson 8 of 13 · 7 min
Preparation of alkenes
NCERT §9.3.4
To make an alkene you either add just one H₂ to an alkyne, or pull a small molecule out of a saturated compound.
The lesson in notes
In short
Partial reduction of alkynes: H₂ over Lindlar's catalyst (palladised charcoal partly poisoned with sulphur compounds or quinoline) gives cis alkenes; sodium in liquid ammonia gives trans alkenes.
Ethyne and propyne add one H₂ over Pd/C to give ethene and propene. Propene shows no geometrical isomerism because one of its doubly bonded carbons carries two H atoms.
Dehydrohalogenation: an alkyl halide heated with alcoholic KOH loses HX to give an alkene. H leaves from the β carbon (next to the carbon bearing X), so this is a β-elimination.
The rate of dehydrohalogenation depends on the halogen (iodine > bromine > chlorine) and the alkyl group (tertiary > secondary > primary).
Dehalogenation: a vicinal dihalide (halogens on adjacent carbons) with zinc loses ZnX₂: CH₂Br–CH₂Br + Zn → CH₂=CH₂ + ZnBr₂.
Acidic dehydration: an alcohol heated with concentrated H₂SO₄ loses water to give an alkene; the –OH removes an H from the β carbon, so this too is a β-elimination.