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Example · Example 13

Q.Suggest two different methods, with equations, to prepare propene, CH3CH=CH2\text{CH}_3\text{CH}{=}\text{CH}_2, in the laboratory.

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Method 1 -- dehydrohalogenation of an alkyl halide. Heating 1-bromopropane with potassium hydroxide dissolved in ethanol (alcoholic KOH favours elimination over the substitution that aqueous KOH would favour) eliminates HBr\text{HBr} across the C1--C2 bond: CH3CH2CH2Br→alc. KOH,ΔCH3CH=CH2+HBr\text{CH}_3\text{CH}_2\text{CH}_2\text{Br} \xrightarrow{\text{alc. KOH},\Delta} \text{CH}_3\text{CH=CH}_2 + \text{HBr}. Method 2 -- acid-catalysed dehydration of an alcohol. Heating propan-1-ol with concentrated sulphuric acid removes a molecule of water across the same two carbons: CH3CH2CH2OH→conc. H2SO4,ΔCH3CH=CH2+H2O\text{CH}_3\text{CH}_2\text{CH}_2\text{OH} \xrightarrow{\text{conc. H}_2\text{SO}_4,\Delta} \text{CH}_3\text{CH=CH}_2 + \text{H}_2\text{O} (alumina at ≈350 °C\approx 350\,°\text{C} works equally well as the dehydrating agent). Both methods remove two atoms/groups from adjacent carbons to generate the double bond; since propan-1-ol/1-bromopropane have only one possible direction of elimination (the leaving group is on a t …

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