ORGANIC SYNTHESIS Flashcards
How do you get from an alkane to halogenalkane?
FREE RADICAL SUBSTITUTION - UV light
How do you get from a halogenalkane to alkene?
ELIMINATION - hot ethanolic NaOH
How do you get from an alkene to a halogenalkane?
ELECTROPHILIC ADDITION - halide/conc h2s04/ Br2
How do you get from a halogenalkane to amine/nitrile/alcohol?
NUCLEOPHILIC SUBSTITUTION
- excess ammonia +heat
- KCN/aqueous NaOH (under reflux)
How do you get from a nitrile to primary amine?
REDUCTION
industry: use nickel catalyst and hydrogen (catalytic hydrogenation)
lab: LiAlH4 in dry ether then dilute acid
How do you get from a primary amine to secondary/tertiary/quaternary ammonium salts?
NUCLEOPHILIC SUBSTITUTION - halogenalkane, heat
How do you get from an alkene to an alcohol?
HYDRATION - phosphoric acid catalyst/ 300oc / 60 atm & steam
How do you get from an alcohol to an alkene?
DEHYDRATION - concentrated sulfuric acid
How do you get from an alcohol to an aldehyde/ketone?
OXIDATION - acidified potassium dichromate - heat(1st)/ reflux (2nd)
How do you get from an aldehyde/ketone to an alcohol?
REDUCTION - NaBH4
How do you get from an aldehyde/ketone to a hydroxynitrile?
NUCLEOHPILIC ADDITION - acidified HCN/ KCN
How do you get from an aldehyde/ketone to a carboxylic acid?
OXIDATION - acidified potassium dichromate (aldehyde only), reflux
How do you get from an alcohol to a carboxylic acid?
OXIDATION - acidified potassium dichromate ( primary alcohol only), reflux
How do you get from a carboxylic acid to an ester?
ESTERIFICATION - concentrated sulfuric acid catalyst and alcohol
How do you get from an ester to a carboxylic acid?
HYDROLYSIS - ACID: dilute acid catalyst (H2SO4)under reflux/BASE: dilute alkaline catalyst (NaOH) under reflux
How do you get from an acyl chloride/acid anhydride to a carboxylic acid?
NUCLEOPHILIC ADDITION-ELIMINATION - water
How do you get from an acyl chloride/acid anhydride to an ester?
NUCLEOPHILIC ADDITION-ELIMINATION - alcohol
How do you get from an acyl chloride/acid anhydride to a primary amide?
NUCLEOPHILIC ADDITION-ELIMINATION - ammonia
How do you get from an acyl chloride/acid anhydride to N-substituted amide?
NUCLEOPHILIC ADDITION-ELIMINATION - amine
How do you get from benzene to nitrobenzene?
NITRATION (ELECTROPHILIC SUBSTITUTION) - concentrated sulfuric acid + nitric acid
How do you get from nitrobenzene to phenylamine?
REDUCTION - Sn + HCl followed by NaOH
How do you get from phenylamine to N-phenylethanamide?
NUCLEOPHILIC ADDITION-ELIMINATION - CH3COCl
How do you get from benzene to phenylketone?
FRIEDEL-CRAFTS ACYLATION: ELECTROPHILIC SUBSITUTION - catalyst: anhydrous AlCl3
