ACYLATION OF AN AROMATIC AMINE
Prepare a solution of 2.5 g of p-toluidine, 65 mL of water, and2.5 mL of concentrated
hydrochloric acid in a 125 mL Erlenmeyer flask. Be sure to placethe reagents in the flask in that
order! Using a warm hot plate to assist you, swirl the contentsof the flask until all of the solid
dissolves. The purpose of the acid is to protonate thep-toluidine and increases its solubility in
water.
In a small beaker, dissolve 3.75 g of sodium acetate trihydratein 7 mL of water. Again,
use a warm hot plate to speed up the process, if necessary. Thepurpose of the sodium acetate is
to buffer the solution. We want the pH such that the carbonylgroup is electrophilic but some of
the amine group is not protonated. A protonated carbonyl groupis more susceptible to
nucleophilic attack, while the amino group can only act as anucleophile when it is not
protonated.
Heat the p-toluidine hydrochloride solution to 50 ?C using a hotplate. While stirring or
swirling rapidly, add 2.5 mL of acetic anhydride from a burettein the hood. Then add the
sodium acetate solution prepared above. Once the solution isthoroughly mixed, cool the flask in
an ice-water bath. A white precipitate should form. Collect thissolid via vacuum filtration.
While the solid is on the filter paper, wash it three times withcold water. After washing the
solid, remove as much of the water from the product by suctionfiltration as possible. Once the
product is fully dry, determine the mass, measure the meltingpoint and calculate the percent
yield. Let your Teaching Assistant evaluate your product anddispose of it properly
please please please please help me do allthese:
calculate the limiting reagent and
the theoretical yield
and the chemical balanced equation
ACYLATION OF AN AROMATIC AMINE
Prepare a solution of 2.5 g of p-toluidine, 65 mL of water, and2.5 mL of concentrated
hydrochloric acid in a 125 mL Erlenmeyer flask. Be sure to placethe reagents in the flask in that
order! Using a warm hot plate to assist you, swirl the contentsof the flask until all of the solid
dissolves. The purpose of the acid is to protonate thep-toluidine and increases its solubility in
water.
In a small beaker, dissolve 3.75 g of sodium acetate trihydratein 7 mL of water. Again,
use a warm hot plate to speed up the process, if necessary. Thepurpose of the sodium acetate is
to buffer the solution. We want the pH such that the carbonylgroup is electrophilic but some of
the amine group is not protonated. A protonated carbonyl groupis more susceptible to
nucleophilic attack, while the amino group can only act as anucleophile when it is not
protonated.
Heat the p-toluidine hydrochloride solution to 50 ?C using a hotplate. While stirring or
swirling rapidly, add 2.5 mL of acetic anhydride from a burettein the hood. Then add the
sodium acetate solution prepared above. Once the solution isthoroughly mixed, cool the flask in
an ice-water bath. A white precipitate should form. Collect thissolid via vacuum filtration.
While the solid is on the filter paper, wash it three times withcold water. After washing the
solid, remove as much of the water from the product by suctionfiltration as possible. Once the
product is fully dry, determine the mass, measure the meltingpoint and calculate the percent
yield. Let your Teaching Assistant evaluate your product anddispose of it properly
please please please please help me do allthese:
calculate the limiting reagent and
the theoretical yield
and the chemical balanced equation
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