Sciencemadness Discussion Board

Sodium Acetate?

imaginary vigil - 7-4-2005 at 06:39

Hi guys. Have only looked at this forum briefly, so I don't know where you're all from, but I'm in Aus and it's late night, and I need help before tomorrow! (BTW, am second year organic chem student.) My question is: I prepared acetanilide from aniline, and sodium acetate was used in the reaction. The question asks what specifically the role of sodium acetate was, but I've no idea. Can anyone help? Cheers!

sparkgap - 7-4-2005 at 06:57

You might want to post the details of the synthesis you did; it's not quite easy telling how something acts if you have no idea how it is used.

sparky (^_^)

imaginary vigil - 7-4-2005 at 07:20

OK.

- Aniline dissolved in water with HCl.
- Acetic anhydride added to this solution of aniline hydrochloride
- When dissolved, it is poured into sodium acetate in water
- Stirred, cooled, and crystals form (of acetanilide).

I'm gathering it's something to do with removal of the hydrochloride, but am not sure.

sparkgap - 7-4-2005 at 07:23

From the looks of things, sodium acetate only served the purpose of neutralizing the excess HCl you had added.

Remember that acetate ion, being the conjugate base of a weak acid, will hydrolyze and produce hydroxide ion in solution.

Hope this helps.

sparky (^_^)

cyclonite4 - 7-4-2005 at 17:11

I agree with sparkgap.

Im no organic chemistry scholar, but I would guess that the acetanilide is the effective byproduct of aniline and acetic anhydride. The sodium acetate is weakly basic and neutralises the HCl. :)