What would be the product formed by this di-ester (see image) with an Na, NH3 solution?
http://imgur.com/7gntqxV

Question

anonymous · Answer

its a reducing agent as far as i remember so if you have some options i can help

anonymous · Answer

@divu.mkr Sorry, there aren't any options given but the answer is supposedly this: http://imgur.com/J4zkohx. I'm not sure how to arrive at it, so any help would be great.

anonymous · Answer

yeah sure... another concept involved is the heating of dicarboxylic acid

anonymous · Answer

are you familiar with it
in the first step both me groups are reduced as predicted
and then heating made that product

anonymous · Answer

Alright, that makes sense. Thanks!

anonymous · Answer

But heating isn't mentioned in the given question. How do we explain that?

photon336 · Answer

@hackpert I can't see your other link

aaronq · Answer

This is a dissolving metal reduction (Birch Reduction), specifically, this is an acyloin condensation. Look here http://www.organic-chemistry.org/namedreactions/acyloin-condensation.shtm

aaronq · Answer

@Photon336 if you remove the "." from the link he posted, you can see the pic http://imgur.com/J4zkohx

photon336 · Answer

Yep I can see this now. This is a birch mechanism.