Nitrationof methyl benzoate - student sheet
n nis expeniment you
benzoate. are going to synthesise a sample of methyl 3-nitrobenzoate by the nitration of methyi
Pre-lab questions
1. Dravw out the skeletal formula for methyl
benzoate.
2. In the nitration of an aromatic compound, the electrophile is the
nitronium ion or nitryl cation, Ci
The nitronium ion is generated in the reaction mixture of concentrated sulfuric acid and
acid.
concerraleá (t:*.
Write anequation/equations toexplain the formation of NO,*from this mixture.
3. Outline a mechanism for the nitration of methyl benzoate to fom methyl
3-nitrobenzoate.
4. The crude product can be purified by recrystallization.
Describe the keyproperties a solvent needs to be suitable for use in recrystallization.
Procedure
Hand protection must be worn
Goggles must be worn
Apparatus Chemicals
conical flasks (1 x 50 cm° and 1 x 100 cm) methyl benzoate (MODERATE HAZARD
balance harmful if swallowed)
spatula concentrated sulfuric acid (CORROSIVE -
causes severe skin burns and eye damage)
10 cm' measuring cylinders x 2
concentrated nitric acid (CORROSIVE AND
glass dropping pipette OXIDISING – causes severe skin burns and
ice-water bath eye damage. May intensify fire)
glass rod methyl 3-nitrobenzoate (no known hazards)
test tube ethanol (FLAMMABLE – highly flammable
liquid and vapour). IDA (FLAMMABLE – highly
thermometer (0100 °C) flammable liquid and vapour; MODERATE
Buchner funnel apparatus HAZARD harmful if swallowed, may cause
damage to organs) can be used instead.
melting point apparatus
distilled water
ROYAL SOCIETY
OF CHEMISTRY
© Royal Society of Chemistry 2016
n nis expeniment you
benzoate. are going to synthesise a sample of methyl 3-nitrobenzoate by the nitration of methyi
Pre-lab questions
1. Dravw out the skeletal formula for methyl
benzoate.
2. In the nitration of an aromatic compound, the electrophile is the
nitronium ion or nitryl cation, Ci
The nitronium ion is generated in the reaction mixture of concentrated sulfuric acid and
acid.
concerraleá (t:*.
Write anequation/equations toexplain the formation of NO,*from this mixture.
3. Outline a mechanism for the nitration of methyl benzoate to fom methyl
3-nitrobenzoate.
4. The crude product can be purified by recrystallization.
Describe the keyproperties a solvent needs to be suitable for use in recrystallization.
Procedure
Hand protection must be worn
Goggles must be worn
Apparatus Chemicals
conical flasks (1 x 50 cm° and 1 x 100 cm) methyl benzoate (MODERATE HAZARD
balance harmful if swallowed)
spatula concentrated sulfuric acid (CORROSIVE -
causes severe skin burns and eye damage)
10 cm' measuring cylinders x 2
concentrated nitric acid (CORROSIVE AND
glass dropping pipette OXIDISING – causes severe skin burns and
ice-water bath eye damage. May intensify fire)
glass rod methyl 3-nitrobenzoate (no known hazards)
test tube ethanol (FLAMMABLE – highly flammable
liquid and vapour). IDA (FLAMMABLE – highly
thermometer (0100 °C) flammable liquid and vapour; MODERATE
Buchner funnel apparatus HAZARD harmful if swallowed, may cause
damage to organs) can be used instead.
melting point apparatus
distilled water
ROYAL SOCIETY
OF CHEMISTRY
© Royal Society of Chemistry 2016
