Organic Synthesis
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What mechanism do alkanes undergo?
free radical substitution
What mechanism do alkenes undergo?
electrophilic addition
What mechanism do alcohols and haloalkanes undergo?
nucleophilic substitution
alkane –> haloalkane
reagent: halogen conditions: UV light reaction: free radical substitution
alkene –> alkane
reagent: H2(g) conditions: Ni catalyst/423K (high temp) reaction: addition/hydrogenation
alkene –> haloalkane
reagent: halogen OR hydrogen halide conditions: room temperature reaction: electrophilic addition/halogenation
alkene –> alcohol
reagent: H20(g) conditions: H3PO4 catalyst reaction: electrophilic addition/hydration
1° alcohol –> aldehyde
reagent: K2Cr2O7 conditions: dilute H2SO4/heat and distil reaction: oxidation
1° alcohol –> carboxylic acid
reagent: K2Cr2O7 conditions: dilute H2SO4/heat under reflux reaction: oxidation
2° alcohol –> ketone
reagent: K2Cr2O7 conditions: dilute H2SO4/heat under reflux reaction: oxidation
alcohol –> alkene
conditions: conc H2SO4 or H3PO4 and heat reaction: elimination/dehydration
alcohol –> haloalkane
reagent: hydrogen halide made in situ NaX + H2SO4 –> HX + NaHSO4 conditions: heat under reflux reaction: nucleophilic substitution
1° haloalkane –> alcohol
reagent: NaOH(aq) or H2O(aq) reaction: nucleophilic substitution/hydrolysis (if water in used as a nucleophile)
what mechanisms do aromatic compounds undergo?
electrophilic substitution
2,4,6 directing groups
activating groups: NH2 OH
3,5 directing groups
deactivating groups: NO2
aldehyde –> 1° alcohol
reagents: NaBH4(aq) reaction: nucleophilic addition
ketone –> 2° alcohol
reagents: NaBH4(aq) reaction: nucleophilic addition
carbonyl –> hydroxynitrile
reagents: 2NaCN + H2SO4 –> 2HCN + Na2SO4 (in situ) reaction: nucleophilic addition
what reactions do carboxylic acids undergo?
• redox (with metals) • neutralisation (with bases) • forms carboxylate ions and salts
carboxylic acid + metal
–> metal carboxylate + hydrogen butanoic acid + Mg –> magnesium butanoate + H2
carboxylic acid + metal oxide
–> metal carboxylate + water butanoic acid + CaO –> calcium butanoate + H2O
carboxylic acid + alkali
–> carboxylate salt + water butanoic acid + NaOH –> sodium butanoate + H2O
carboxylic acid + metal carbonate
–> carboxylate salt + carbon dioxide + water butanoic acid + MgCO3 –> magnesium butanoate + CO2 + H2O