organic syntheis Flashcards
Alkane to Haloalkane
UV light and X2 (halogen)
FRS
Haloalkane to Alkene
KOH, ethanol, reflux
Elimination
Haloalkane to Alcohol
warm NaOH, Reflux
Nucleophilic substitution
Haloalkane to Nitrile
KCN, Ethanol, reflux
Nucleophilic substitution
Haloalkane to Primary Amine
Ammonia, heat. (primary haloalkanes only)
Nucleophilic substitution
Haloalkane to secondary/tertiary amines their salts and quaternary ammonium salts
ammonia, heat
not primary haloalkanes
nucleophilic substitutions
Nitrile to Primary amine
LiAlH4, dilute H2SO4
reduction
alkene to dibromialkane (test for unsaturation c=c)
Br2
20 degrees
Alkene to alcohol
H3PO4 catalyst
steam
300 degrees
60 atm
this is “hydration of alkene”
or
H2O, H2SO4 catalyst
electrophilic addition
Alkene to Haloalkane
H-halogen e.g. H-Br
20 degrees
electrophilic addition
Alcohol to Alkene
conc H2SO4, reflux
elimination
Alcohol to aldehyde/ketone
Acidified potassium dichromate (K2Cr2O7,H2SO4)
heat in distillation
not tertiary alcohols
oxidation
Alcohol to Carboxylic acid
Acidified potassium dichromate (K2Cr2O7/H2SO4)
reflux
oxidation
primary alcohols only
Aldehyde/ketone to Alcohol
NaBH4 in water with methanol
Nucleophilic addition
reduction
Aldehyde/ketone to Hydroxynitrile
KCN, H2SO4,
20 degrees
Nucleophilic Addition
aldehyde/ketone to carboxylic acid
Acidified potassium dichromate (K2Cr2O7/H2SO4)
Reflux
Oxidation
Carboxylic acid to ester
alcohol, concentrated H2SO4 catalyst, heat
called an esterification reaction
Ester to carboxylic acid
dilute H2SO4 catalyst
H2O
reflux
(acid hydrolysis)
Acyl Chloride/Acid anhydride to Ester
Alcohol
20 degrees
vigorous reaction
Acyl chloride/Acid Anhydride to Primary amide
violent reaction
NH3
20 degrees
Acyl chloride/Acid anhydride to N-substituted Amide
primary amine
20 degrees
Benzene to nitrobenzene
Nitration
Electrophilic substitution
conc H2SO4, Conc HNO3
below 55 degrees
Benzene to phenylketone
Friedel crafts acylation
Electrophilic substitution
RCOCL
AlCl3 catalyst
reflux
non aqueous environment
Nitrobenzene to an aromatic amine
reduction
tin, concentrated HCl
reflux
add NaOH
Aromatic amine to N-Phenylethanamide
CH3COCl