reaction pathways of aliphatic compounds Flashcards
NOP = non-organic product
alkane -> haloalkane
- conditions: halogen, UV radiation
- reaction: free radical substitution (learn steps)
- NOP: HX (g)
alkene -> alkane
- conditions: H₂ / Ni
- reaction: hydrogenation (addition)
alkene -> dihaloalkane
- conditions: X₂
- reaction: halogenation (addition)
alkene -> alcohol
- conditions: H₂O (steam) / H₃PO₄
- reaction: hydration (addition), 2 possible products
alkene -> haloalkane
- conditions: hydrogen halide
- reaction: electrophilic addition (know mechanism)
haloalkane -> alcohol
- conditions -: NaOH (aq)
- reaction: nucleophilic substitiution (hydrolysis, know mechanism)
- NOP: X-
haloalkane -> amine
- conditions: NH₃ / ethanol, NaOH to liberate amine from salt
- NOPs: NaCl + H₂O
haloalkane -> nitrile
- conditions: NaCN / ethanol
- reaction: nucleophilic substitution (know mechanism)
- NOP: X-
primary alcohol -> aldehyde
- conditions: K₂Cr₂O₇ / H₂SO₄, distillation
- reaction: oxidation
- NOP: H₂O
primary alcohol -> carboxylic acid
- conditions: K₂Cr₂O₇ / H₂SO₄, reflux
- reaction: oxidation, have 2 [O] in equation
- NOP: H₂O
secondary alcohol -> ketone
- conditions: K₂Cr₂O₇ / H₂SO₄, reflux
- reaction: oxidation
- NOP: H₂O
alcohol -> alkene
- conditions: H₃PO₄ or H₂SO₄, heat under reflux
- reaction: dehydration (elimination)
alcohol -> haloalkane
- conditions: sodium halide / H₂SO₄, heated under reflux, which forms a hydrogen halide in situ
- reaction: substitution
- NOP: H₂O
alcohol -> ester
- conditions: carboxylic acid / conc. H₂SO₄ OR acid hydride
- reaction: esterification
- NOP: H₂O
aldehyde -> primary alcohol
- conditions: NaBH₄ / H₂O
- reaction: reduction, 2 [H] in equation (know mechanism)
aldehyde -> carboxylic acid
- condtions: K₂Cr₂O₇ / H₂SO₄, reflux
- reaction: oxidation
aldehyde -> hydroxynitrile
- conditions: NaCN (aq) / H+ (aq) - these make HCN
- reaction: nucleophilic addition (know mechanism)
ketone -> secondary alcohol
- conditions: NaBH₄ / H₂O
- reaction: reduction, 2 [H] in equation (know mechanism)
ketone -> hydroxynitrile
- conditions: NaCN (aq) / H+ (aq) - these make HCN
- reaction: nucleophilic addition (know mechanism)
aldehyde / ketone -> hydroxynitrile
- conditions: HCN
- reaction: nucleophilic addition (know mechanism)
carboxylic acid -> carboxylate
- redox reactions with metals
- neutralisation reactions with bases (alkalis, metal oxides, and carbonates)
carboxylic acid -> ester
- conditions: alcohol / conc. H₂SO₄
- reaction: esterification
- NOP: H₂O
carboxylic acid -> acyl chloride
- conditions: SOCl₂
- NOPs: SO₂ (g), HCl (g)
carboxylic acid -> acid anhydride
- reactants: 2 CAs
- NOP: H₂O
ester -> carboxylic acid (+ alcohol)
- conditions: heated under reflux with dilute aqueous acid
- reaction: acid hydrolysis, reversible
- put H₂O as reactant in equation
ester -> carboxylate (+ alcohol)
- conditions: heated under reflux with aqueous hydroxide ions
- reaction: alkaline hydrolysis, irreversible
- put OH- as reactant in equation
acyl chloride -> ester
- conditions: alcohol
- NOP: HCl
acyl chloride -> carboxylic acid
- conditions: H₂O
- NOP: HCl
acyl chloride -> primary amide
- conditions: NH₃
- NOP: NH₄Cl (ammonium chloride)
acyl chloride -> secondary amide
- conditions: primary amine
- other product: alkylammonium chloride (eg. CH₃NH₃⁺Cl⁻)
nitrile -> amine
- conditions: H₂ / Ni
- reaction: reduction
nitrile -> carboxylic acid
- conditions: H₂O / HCl, heat
- NOP: NH₄Cl
hydroxynitrile -> carboxylic acid
- conditions: H₂O / HCl, heat
- NOP: NH₄Cl
hydroxynitrile -> amine
- conditions: H₂ / Ni
- reaction: reduction
