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AH Chemistry... need help

Is this an ester?

CH3COOCH2CH2OOCH3

I can't work it out. The question is comes from is:

What would be the products formed when CH3COOCH2CH2OOCCH3 is warmed with aqueous sodium hydroxide solution?

The answer is:

CH3COONa + HOCH2CH2OH

According to the answer, 4 Carbons are accounted for, yet in the original molecule there are 6. I'm confused

Reply 1

thelostchild

there are two ester bonds in that molecule so you would form 2 molecules of Sodium Ethanoate (CH3COONa)

Reply 2

ixivxivi

Oi! I just came on TSR for a break from a morning of organic chem revision! And you made me log on - I'd been very good and kept logged out as a deterent from procastionation!

Anyway, I think it follows the reaction I've drawn in the attachment... You go from 5 to 5 - you have your ester, then you get CH3COOH and -OCH2COOH and -OMe as you should be able to see in the attachment :smile:

. Then there is a way to get rid of the carbonyl group on the -OCH2COOH... I think you'd either reduce it to an alcohol either using LiAlH4, LiBH4 or (i-PrO)3Al, but all these would reduce the carbonyl you've got on the other atom which you want to keep... So I'm not entirely sure how you'd get rid of the carbonyl...

EDIT: ooh, and forgot to say that the -OH won't add simultaneously to both carbonyl groups as shown, but rather in the order of which carbonyl group is the more reactive, but I'm not entirely sure which this is...

tsr chem prob.jpg16.9KB

Reply 3

ixivxivi

And you should get the Na+ bits by swapping around protons and sodium ions? And I should warn you, I'm naff at Organic chem, am probably going to fail my paper in two weeks etc etc

Also, isn't that really, really complicated for Advanced Higher Chemistry? or does the AH stand for something different?

I've attached to this the structures of the products I think you want...