Question

In the reformatsky reaction, why doesn't the ester in the final product get hydrolysed even though we use H3O+?

Answer 1

H3O+ is a fairly weak acid (I think pKa ~1.7) and the product formed by reformatsky reactions are not very reactive itself. It might require a fairly stronger acid to hydrolize the ether.

Answer 2

Oh, okay! Thank you!

Answer 3

I wouldn't say 1.7 pKa is a weak acid if anything it is moderately strong.

The reason hydrolysis does not occur could be for a variety of reasons,

1. Esters are not very electrophilic, (look at the resonance structures of esters)
2. Only enough acid is utilized to allow cleavage of the Zink, thus you can control the amounts of acid to minimize the amount of product hydrolyzed

Answer 4

Okay, one more in Organic chem:
how does (CH3)2CuLi react with

Answer 5

H3O+ is a fairly weaker acid compared to HCl, HBr, and of course Sulfuric Acid. I didn't say it was a really weak acid. But it is stronger than say, NH4Cl.

Answer 6

^^ My question! Please! Somebody!

Answer 7

I believe this is a gilman reagent. If I remember correctly, it's a nucleophilic attack on alpha, beta unsaturated carbonyl compounds. they add the alkyl group to the beta carbon.
So it would add to the C2

Answer 8

okayy!