419180
Know the main synthetic routes and
reactivity for furans, pyrroles and
thiophenes thiophenes
- Furans
- Synthesis
- Dehydrated 1,4 carbonyl compounds
- Carbonyls protonated
- Alcohol reacts with =O+H and a five membered ring forms with one alcohol group
- Loss of water, carbonyl acidified at beginning
- Loss of water, carbonyl acidified at beginning
- Alcohol reacts with =O+H and a five membered ring forms with one alcohol group
- Carbonyls protonated
- Dehydrated 1,4 carbonyl compounds
- Source
- Carbohydrate waste
- Ribose/furanose structures
- furfural
- furan
- furan
- furfural
- Ribose/furanose structures
- Carbohydrate waste
- Reactivity
- Nitration
- Nitric acid and sulphuric acid
- polymeric resin
- polymeric resin
- Acetyl nitrate
- NO2 and AcO attached to 2 and 5 positions
- OAc group lost when reacted with pyridine
- OAc group lost when reacted with pyridine
- NO2 and AcO attached to 2 and 5 positions
- Nitric acid and sulphuric acid
- Bromination
- Br2, RT
- Polybromination
- Polybromination
- Br2, dioxane
- Br at 2 position
- Br at 2 position
- Br2, EtOH, -40oC
- OEt at 2 and 5 position
- Mechanism
- monobromine sub
- EtOH reacts at double bond adjacent to positive O atom
- Loss of bromine atom
- Addition of another EtOH group
- Addition of another EtOH group
- Loss of bromine atom
- EtOH reacts at double bond adjacent to positive O atom
- monobromine sub
- Mechanism
- OEt at 2 and 5 position
- Br2, RT
- Diels-Alder
- Nitration
- Synthesis
- Pyrroles
- Synthesis
- Paul Knorr
- 1,4 dicarbonyl and amine
- Mechanism
- Addition of amine to C=O and protonation of C=O
- Loss of water
- Movement of double bond
- Ring closing
- Loss of water
- Loss of water
- Ring closing
- Movement of double bond
- Loss of water
- Addition of amine to C=O and protonation of C=O
- Mechanism
- 1,4 dicarbonyl and amine
- Hantzsch
- 1,4 dicarbonyl, haloketone and amine
- Loss of water and HCl
- Loss of water and HCl
- 1,4 dicarbonyl, haloketone and amine
- Paul Knorr
- Reactivity
- Electrophilic substitution
- v. reactive
- 2, 3 posititons
- Tetrabromination
- v. reactive
- Acid sensitive
- v. weak base
- lone pair on N used in 6 pi system
- lone pair on N used in 6 pi system
- Deprotection with base
- Can be alkylated at C or N
- Use alkyl halide
- Use alkyl halide
- Can be alkylated at C or N
- Diels-Alder
- Needs N-EWG and highly reactive dienophile
- Needs N-EWG and highly reactive dienophile
- Electrophilic substitution
- Synthesis
- Thiophene
- Synthesis
- 1,4 dicarbonyl, P2S5, 170oC
- 1,3-diyne and metal sulphide, NaSH, EtOH
- 1,4 dicarbonyl, P2S5, 170oC
- Reactivity
- Electrophilic aromatic substitution
- Most aromatic of 3
- Most aromatic of 3
- Not acid sensitive
- No diels alder
- Friedel Crafts
- Bromination at 2 position
- Desulfurisation
- Dehydrogenation carbon skeleton
- Raney Nickel catalyst
- Al/Ni alloy dissolved in aq. NaOH
- Leaves sponge of fine particles with H2 absorbed
- Leaves sponge of fine particles with H2 absorbed
- Al/Ni alloy dissolved in aq. NaOH
- Dehydrogenation carbon skeleton
- Electrophilic aromatic substitution
- Synthesis
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