[helplessperson]

I have attached the screenshots of the problems below. I am not sure where to start.

1. I am guessing that an Claisen reaction should be used somewhere in here but I cannot start. the alpha carbon does not have 2 alpha protons for use in any of the reactants. I cannot do any Michael Addition either because of this reason. I can't make sense of the hint either... The ethoxide plays two role, one role I'm assuming is in Claisen addition, but I cannot think of anything else.
2. This one is just plain confusing. No alpha protons for me to work with anywhere... I don't think this is an intramolecular claisen either.

What's tripping me up is how to deal with these double bonds in both these problems.

If anyone can just point me in the right direction that'll be a huge help. I'd really appreciate it if you can tell me the intermediates are of these problems,

[Babcock_Hall]

In the top reaction what two roles do you think that ethoxide ion might play?

[helplessperson]

I think one role is in Claisen, where it is kicked off the molecule during the reaction. The second role is acting as a base to deprotonate the only alpha proton available... but I dont think this is what the hint was aiming at. Even if these are correct, I am not sure what to do since Aldol and Claisen requires 2 alpha proton for it to go through in my knowledge.

[helplessperson]

What two roles do you think that ethoxide ion might play?

Would Ethoxide play these two roles? I'm thinking I only got one of them -- ethoxide plays a role in Claisen...  but ethoxide acting as a base could be wrong.

[Babcock_Hall]

Besides being a base, what other general property does ethoxide have?

[helplessperson]

Besides being a base, what other general property does ethoxide have?

I think I understand now... ethoxide will add to the beta position of the alpha-beta unsaturated molecule, pushing the negative charge onto the alpha carbon position. This negative charge will attack and perform aldol condensation with the other molecule. The result is the target. Thank you


As for the second, how should I start? I started by adding OH- to the beta position on the right side, pushing the negative charge onto the alpha carbon. Then, this negative charge would resonate and now there's a negative charge on the Oxygen atom.

[Babcock_Hall]

I would cast my net broadly.  Hydroxide has what chemical properties?

[helplessperson]

I would cast my net broadly.  Hydroxide has what chemical properties?

OH is also a base which leads me to deprotonate the alpha proton on either side. The negative charge resulting could resonate onto the ring and delocalized onto the oxygen atom. Is the way to go? I've been trying various ideas now for half an hour but nothing seems to work...

[Babcock_Hall]

Which proton is most acidic, and why?

[helplessperson]

Which proton is most acidic, and why?

I'm assuming its the proton at the para position. If it is, then it would just resonate onto the ring and push the negative charge onto the oxygen atom. At this point, the oxygen would just accept a proton from the H and it's the product.

[Babcock_Hall]

I am not sure what you intend to be the proton donor, but I think that you are on the right track.

[helplessperson]

I am not sure what you intend to be the proton donor, but I think that you are on the right track.

Forgive me. I was too suprised at my stupidity to type out H2O out fully.