Ethanol is dehydrated to ethene using concentrated H₂SO₄. Ethene is converted to ethyne by bromination followed by dehydrohalogenation. Ethyne reacts with NaNH₂ to form sodium acetylide, which then reacts with ethyl bromide to form but-1-yne.

Ethane undergoes free radical bromination with Br₂/hv to form bromoethane. Bromoethane undergoes dehydrohalogenation with alcoholic KOH to form ethene. Ethene is then brominated and dehydrohalogenated to form bromoethene.

Propene undergoes anti-Markovnikov addition of HBr in presence of peroxide to form 1-bromopropane. 1-Bromopropane reacts with AgNO₂ to form 1-nitropropane.

Toluene undergoes side-chain chlorination with Cl₂ in presence of light to form benzyl chloride. Benzyl chloride is hydrolysed with aqueous NaOH to form benzyl alcohol.

Propene reacts with HBr to form 2-bromopropane. 2-Bromopropane undergoes double dehydrohalogenation with alcoholic KOH to form propyne.

Ethanol reacts with PBr₃ or HBr to form ethyl bromide. Ethyl bromide undergoes Swarts reaction with AgF to form ethyl fluoride.

Bromomethane reacts with Mg in dry ether to form methyl magnesium bromide (Grignard reagent). This reacts with acetyl chloride followed by hydrolysis to form propanone.

But-1-ene undergoes addition of HBr to form 2-bromobutane. 2-Bromobutane undergoes dehydrohalogenation with alcoholic KOH to form but-2-ene.

1-Chlorobutane undergoes Wurtz reaction with sodium metal in dry ether to form n-octane.

Benzene undergoes electrophilic substitution with Cl₂ in presence of Fe/FeCl₃ to form chlorobenzene. Chlorobenzene undergoes Ullmann coupling with Cu to form biphenyl.