Organic Synthesis Flashcards
alcohol → aldehyde
acidified K₂Cr₂O₇
heat in distillation
(1° alcohol)
alcohol → carboxylic acid
acidified K₂Cr₂O₇
reflux
oxidation
alcohol → ketone
acidified K₂Cr₂O₇, reflux
oxidation (2° alcohol)
aldehyde → alcohol
NaBH₄ in methanol + water
nucleophillic addition (reduction)
ketone → alcohol
NaBH₄ in methanol + water
nucleophillic addition (reduction)
alcohol → alkene
concentrated H₂SO₄ or H₃PO₄
reflux
elimination/dehydration
alkene → alcohol
steam
H₃PO₄ catalyst
60atm, 300°C
alcohol → haloalkane
sodium halide
H₂SO₄, 20°C
haloalkane → alcohol
NaOH aq.
heat under reflux
nucleophillic substitution
alkane → haloalkane
halogen
UV light
free radical substitution
alkene → haloalkane
hydrogen halide
room temperature
electrophillic addition
alkene → dihaloalkane
halogen
room temperature
electrophillic addition
alkene → alkane
hydrogen
nickel catalyst, 150°C
hydrogenation
haloalkane → nitrile
ethanolic + aqueous KCN
heat under reflux
nucleophillic substitution
haloalkane → alkene
ethanolic OH-
heat under reflux
elimination
nitrile → primary amine
LiAlH₄ in dry ether
heat
(or H2 + nickel catalyst)
reduction
haloalkane → primary amine
excess ammonia
heat under pressure
nucleophillic substitution
haloalkane → quaternary ammonium salt
ammonia
heat under pressure
nucleophillic substitution
aldehyde/ketone → hydroxynitrile
KCN, H₂SO₄
room temperature
nucleophillic addition
acyl chloride / acid anhydride → carboxylic acid
H₂O
room temperature
nucleophillic addition elimination
acyl chloride / acid anhydride → primary amide
ammonia
room temperature
nucleophillic addition elimination
acyl chloride / acid anhydride → ester
alcohol
room temperature
nucleophillic addition elimination
carboxylic acid → ester
alcohol + H₂SO₄
heat & catalyst?
esterification/condensation
ester → carboxylic acid
1) dilute H₂SO₄ , H₂O
reflux, catalyst
acidic hydrolysis
OR
2) aqueous NaOH
reflux
alkaline hydrolysis (forms carboxylate salt)
ester → carboxylic acid
1) dilute H₂SO₄ , H₂O
reflux, catalyst
acidic hydrolysis
OR
2) aqueous NaOH
reflux
alkaline hydrolysis (forms carboxylate salt
acyl chloride / acid anhydride → N - substituted amide
amine
room temperature
nucleophillic addition elimination
carboxylic acid → carboxylate salt
aq NaOH
room temperature
acid - base
benzene → nitrobenzene
concentrated H₂SO₄ + HNO₃
25 - 60°C
electrophillic subsitution
nitrobenzene → phenylamine
concentrated HCl + Sn
heat
reduction
phenylamine → N-phenylethanamide
acyl chloride
room temperature
nucleophillic addition elimination
benzene → phenylketone
acyl chloride
anhydrous AlCl₃
electrophilic substitution
