Reaction Help

en.wikipedia.org/wiki/Ionic_bonding
read 6th section

>using sodium hydroxide to break down a carboxylate into carbonate and a carbanion leaving group

Holy shit

>using sodium hydroxide to break down a carboxylate into carbonate and a carbanion leaving group
what is it

If you mean the comparison with covalent bonding section, that doesn't show ionic bonding is a special case of covalent. It shows bonding is a spectrum with the idealised ionic bond at one end and the idealised covalent bond at the other, and bonds in real life fall in between.

I mean that the ionic bond is an extreme case of polarization of the covalent polar bond. And the fact that in the picture the ionic bond is shown as covalent, it's because the program draws covalent bonds by default, and I'm lazy to change something.

Or the covalent bond is an extreme case of electron sharing for the ionic bond

That's a fair enough reason to draw it that way, I was just nitpicking tbf

It's good that you understand. Because I didn't really understand what you meant to say
>If you mean the comparison with covalent bonding section, that doesn't show ionic bonding is a special case of covalent. It shows bonding is a spectrum with the idealised ionic bond at one end and the idealised covalent bond at the other, and bonds in real life fall in between.
my English is bad

Are we talking catalyst in a single step? Because no way a C-C bonds reacts before a C=C bond

The oxidation into decarboxylation cascade seems cool, although I would use a Krapcho decarboxylation

Also thats called a vinyl group

Imagine two particles where the electronegativity difference is infinite. That's a completely ionic bond, which you'll never find actually existing. Imagine two particles where the electronegativity difference is zero, like in a diatomic molecule with identical particles, like the halogens. That's your idealised covalent bond, which obviously does exist in nature. Every other bond in nature falls somewhere in between these two bonds with respect to the degree of electron sharing.

Thank you, now I understand

As soon as hydroxide reacts with carboxylate a intermediate state is created.

In this intermediate state C-C σ* is much higher in energy than C-O σ*
Since we are using O- np that acts as a nucleophile and HOMO, it will react with C-O σ* LUMO.

In Lewis structure rational, we would say that OH or ONa are much better leaving groups than R.

I appreciate any constructive criticism if you see any errors in my explanation..

Thanks for the explanation, but it was understandable. I did not notice that the different anonyms are ask and I thought that it was still about bonds.

you are right is absolute bullshit

Malonic ester synthesis is cheaper and simpler

What is R tho

>I would use a Krapcho decarboxylation

That's not going to work because of Also, why would you use Krapcho, sodium hydroxide not good enough for you?

Since it's not specified we can assert that it's not important to the overall reaction. Something like simple alkyl group i would assume.

Don't want to use expensive base when there is no need ;)

Honestly I just have better experiences with Krapcho

>expensive base
>sodium hydroxide

Enjoy separating your product from all the gloopy DMSO