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Mechanism between sodium ethanoate and ethanoyl chloride

I know the product is ethanoic anhydride, but is there a mechanism or could someone describe to me the mechanism?
Original post by ps1265A
I know the product is ethanoic anhydride, but is there a mechanism or could someone describe to me the mechanism?


It looks like nucleophilic substitution at the carbonyl group with the chloride a leaving group.
Reply 2
Avatar for Hudl
Hudl
16
Original post by ps1265A
I know the product is ethanoic anhydride, but is there a mechanism or could someone describe to me the mechanism?


Yeah,

As the O&-Na&+ bond is ionic, in aqueous conditions the Na&+ ion will dissociate allowing the O from the rest of the chain to act as a nucleophille.

The reaction is an Addition elimination reaction.
(edited 9 years ago)
ps1265A help.png5.9KB
Original post by Hudl
Yeah,

As the O&-Na&+ bond is ionic, in aqueous conditions the Na&+ ion will dissociate allowing the O from the rest of the chain to act as a nucleophille.

The reaction is an Addition elimination reaction.


Aqueous conditions will decompose the ethanoyl chloride ...

The mechanism is nucleophilic substitution.
I agree, it's nucleophilic substitution not addition-elimination
Reply 5
Avatar for Hudl
Hudl
16
Original post by charco
Aqueous conditions will decompose the ethanoyl chloride ...

The mechanism is nucleophilic substitution.


Okay please further explain, the O and Na bond is ionic? How do they dissociate to allow the O to act as a nucleophile and also how do you differ an addition elimination reaction to a nucleophilic substitution reaction?

Have I done the actual mechanism right?
(edited 9 years ago)
Original post by Hudl
Okay please further explain, the O and Na bond is ionic? How do they dissociate to allow the O to act as a nucleophile and also how do you differ an addition elimination reaction to a nucleophilic substitution reaction?

Have I done the actual mechanism right?




Yes, your mechanism is correct.

The driving force behind the mechanism is nucleophilic attack and the overall effect is substitution.

You can also call it nucleophilic addition-elimination.

The reaction is best carried out under anhydrous conditions in diethylether (ethoxyethane).

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