28 - organic synthesis Flashcards
name of mechanism + reagents + conditions
alkane to haloalkane
free radical substitution
halogen / hydrogen halide
UV light
name of mechanism + reagents + conditions
alkene to alkane
electrophilic addition
Hydrogen
nickel catalyst
name of mechanism + reagents + conditions
alkene to haloalkane
electrophilic addition
hydrogen halide / hydrogen
name of mechanism + reagents + conditions
haloalkane to nitrile ???
nucleophilic substitution
CN- / NaCN
ethanol
name of mechanism + reagents + conditions
haloalkane to amine ???
nucleophilic substitution
NH3 + NaOH
ethanol
name of mechanism + reagents + conditions
alkene to alcohol
hydration
steam
phosphoric acid catalyst
name of mechanism + reagents + conditions
alcohol to alkene ??
dehydration
hot conc sulfuric acid catalyst
reflux
name of mechanism + reagents + conditions
haloalkane to alcohol
nucleophilic substitution
aqueous NaOH
reflux
name of mechanism + reagents + conditions
alcohol to haloalkane
2 step mechanism
sodium halide
sulfuric aid
reflux
name of mechanism + reagents + conditions
alcohol to ketone
oxidation
secondary alcohol
sulfuric acid (H+)
K2Cr207
reflux
name of mechanism + reagents + conditions
ketone to hydroxynitrile
nucleophilic addition
aqueous NaCN
H+
name of mechanism + reagents + conditions
hydroxynitrile to amine
reduction
hydrogen
nickel catalyst
name of mechanism + reagents + conditions
alcohol to aldehyde
oxidation
primary alcohol
sulfuric acid / H+
K2Cr2O7
distillation
name of mechanism + reagents + conditions
ketone to alcohol
nucleophilic addition
forms secondary alcohol
aqueous NaBH4
name of mechanism + reagents + conditions
aldehyde to alcohol
nucleophilic addition
aqueous NaBH4
warmed
name of mechanism + reagents + conditions
alcohol to carboxylic acid
oxidation
primary alcohol
sulfuric acid / H+
K2Cr2O7
reflux
name of mechanism + reagents + conditions
aldehyde to carboxylic acid
oxidation
sulfuric acid / H+
K2Cr2O7
reflux
name of mechanism + reagents + conditions
aldehyde to hydroxynitrile
nucleophilic addition
aqueous NaCN
H+
name of mechanism + reagents + conditions
nitrile to carboxylic acid
hydrolysis
H20
HCl
heat
name of mechanism + reagents + conditions
alcohol to ester
esterification
carboxylic acid
conc sulfuric acid
OR
acid anhydride
name of mechanism + reagents + conditions
nitrile to amine
reduction
hydrogen
nickel catalyst
name of mechanism + reagents + conditions
ester to carboxylic acid ??
aq acid hydrolysis
dilute acid
reflux
name of mechanism + reagents + conditions
ester to carboxylate ??
alkaline hydrolysis
OH-
reflux
name of mechanism + reagents + conditions
carboxylic acid to ester
esterification
alcohol
conc sulfuric acid
warmed
name of mechanism + reagents + conditions
carboxylic acid to acyl chloride
chlorination
SOCl2?
fume hood
name of mechanism + reagents + conditions
acyl chloride to carboxylic acid
hydrolysis
nucleophilic addition - elimination
H20
name of mechanism + reagents + conditions
acyl chloride to ester
nucleophilic addition elimination
alcohol
name of mechanism + reagents + conditions
acyl chloride to primary amide
nucleophilic addition -elimination
NH3
name of mechanism + reagents + conditions
Acyl chloride to secondary amide
nucleophilic addition-elimination
primary amine
name of mechanism + reagents + conditions
hydroxynitrile to carboxylic acid
hydrolysis
H20
HCl
heat
name of mechanism + reagents + conditions
nitriles to amines
reduction
hydrogen
nickel catalyst
name of mechanism + reagents + conditions
nitriles to carboxylic acids
hydrolysis
dilute HCl
heat
name of mechanism + reagents + conditions
ketone/aldehyde to alcohol
nucleophilic addition
Grignard reagent
followed by dilute aq acid (HCl)
name of mechanism + reagents + conditions
benzene to bromobenzene
electrophilic substitution
Br2
halogen carrier catalyst - AlBr3
room temp + pressure
name of mechanism + reagents + conditions
benzene to chlorobenzene
electrophilic substitution
Cl2
halogen carrier catalyst - AlCl3
room temp + pressure
name of mechanism + reagents + conditions
benzene to benzaldehyde
electrophilic substitution
acyl chloride
halogen carrier catalyst
name of mechanism + reagents + conditions
benzaldehyde to benzoic acid
reduction?
NaBH4 (aq)
name of mechanism + reagents + conditions
benzene to methylbenzene
electrophilic substitution
haloalkane
halogen carrier catalyst
name of mechanism + reagents + conditions
benzene to nitrobenzene
electrophilic substitution
conc HNO3
conc H2SO4
50 degree water bath
name of mechanism + reagents + conditions
nitrobenzene to phenylamine
reduction
tin / conc HCl
reflux??
followed by excess NaOH
name of mechanism + reagents + conditions
phenol to sodium phenoxide
electrophilic substitution?
neutralisation?
NaOH
name of mechanism + reagents + conditions
phenol to nitrophenol
electrophilic substitution
dilute HNO3
room temp
name of mechanism + reagents + conditions
phenol to 2,4,6 - tribromophenol
electrophilic substitution
bromine
what are Grignard reagents
Organometallic compounds that provide a source of nucleophiles called carbanions
(C has a negative charge)
example of a Grignard reagents
CH3CH2MgBr
