[mana]

hi all
I have tried to synthesis acetanilide by this procedure, but I didn't achieve any participate, where is my mistake?
Place 70 mL of deionized/distilled H2O into 250 mL Erlenmeyer flask &then add 5.0 g aniline with 4.5 mL conc. HCl and heated for 10 min in water batch

-- In 125 mL flask, place 4.5 g of sodium acetate + 10 mL H2O

- Add 5 mL of acetic anhydride to aniline soln then stir and heat in water batch for 10 min again

- Add sodium acetate solution to aniline solution + stir and heat 10 min more

after these steps I placed the flask into ice water batch and scratched it but I didn't achieved any participate? where is my mistake?
and also one more question what is the sodium acetate rule here?

[chenbeier]

Probably the solution is stil to diluted for getting a precipitate. The sodium acetate exchange I think the chloride.

[mana]

hi all
I have tried to synthesis acetanilide by this procedure, but I didn't achieve any participate, where is my mistake?
Place 70 mL of deionized/distilled H2O into 250 mL Erlenmeyer flask &then add 5.0 g aniline with 4.5 mL conc. HCl and heated for 10 min in water batch

-- In 125 mL flask, place 4.5 g of sodium acetate + 10 mL H2O

- Add 5 mL of acetic anhydride to aniline soln then stir and heat in water batch for 10 min again

- Add sodium acetate solution to aniline solution + stir and heat 10 min more

after these steps I placed the flask into ice water batch and scratched it but I didn't achieved any participate? where is my mistake?
and also one more question what is the sodium acetate rule here?

is it because heating aniline with HCl ? I mean is it possible that aniline has been protonated and inactivated, thus it can not react with anhydride acetic, also when I checked the procedure it doesn't need to heat in any steps, but I can't guess that does heat affected the reaction or not?

[PKa]

I would change the sequence of addition: Aniline in water, then acetic anhydride followed by Conc. HCl then heated in water bath.