Organic Synthesis Flashcards
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
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)
conditions: heat under reflux
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
NHR