Pharmaceutcal Synthesis Flashcards
How do you form an alcohol?
A halogenoalkane with NaOH/H2O under reflux.
Reduce a ketone or aldehyde with NaBH4.
Ketone –> secondary
Aldehyde –> primary. (Warm together)
How do you form a primary aliphatic amine?
-NH2
Eg propyl amine
Halogenoalkane + excess NH3 and an ethanol solvent.
1-chloropropane + NH3 —>
Propyl amine + HCl
How do you form a ketone?
Oxidise a secondary alcohol with K2Cr2O7/H+
Forms H2O as a bi product.
How do you form an aldehyde?
Oxidise a primary alcohol with K2Cr2O7/H+
Also forms H2O as a bi product.
How do you form a carboxylic acid?
Oxidise an aldehyde with K2Cr2O7/H+
How do you form an ester?
React a carboxylic acid and an alcohol together with a H2SO4 catalyst under reflux.
How do you make chlorobenzene or Bromobenzene?
Catalyst equation?
Benzene + Br2 Fe/AlBr3
+ Cl2 Fe/AlCl3
Also creates HCl or HBr
Br2 + FeBr3 —> Br+ + FeBr4-
H+ + FeBr4- —> FeBr3 + HBr
How do you make nitrobenzene?
Benzene
Conc HNO3
Conc H2SO4
50*
Also creates H2O
How is H2SO4 used as a catalyst to make nitrobenzene?
HNO3 + H2SO4 —>
NO2+ + HSO4- + H2O
H+ + HSO4- —> H2SO4
How do you make phenyl amine?
Nitrobenzene + 6 [H] —>
Phenyl amine + 2H2O
Sn/conc HCl are the reducing agent.
Reflux.
How do you make benzenediazonium chloride?
Phenyl amine + HNO2 + 2HCl —>
Benzenediazonium chloride + 2H2O
HNO2 + NaCl
How do you form an azo dye?
Benzenediazonium chloride + phenol + NaOH —>
Azo dye
Alkaline conditions
How do you form an amine without producing the further substitution?
Eg make 3-aminopropan-1-ol
Excess NH3 ethanol solvent under reflux.
3-chloropropan-1-ol + 2NH3 —>
3-aminopropan-1-ol + NH4Cl
How do you separate from forming an aldehyde or carboxylic acid when using a primary alcohol?
Distil the aldehyde from the reaction mixture as it forms, this prevents it being oxidised further to a carboxylic acid.
When making a carboxylic acid you heat the reaction mixture under reflux before distilling the product off.
