Double bonds, amalgams and alklis
While researching some routes of synthesis of malonic acid grom glycerol, I ran at some interesting reactions:
1. Acrolein and HCl - anti-Markovnikov addition?
https://en.wikipedia.org/wiki/Hydrohalogenation
So, I'm referencing an the reaction at the bottom of page. Looks like that anti-Markovnikov addition is due to acrolein being Michael acceptor.
2. Acrylic acid and alkali
http://orgsyn.org/demo.aspx?prep=CV1P0321
In segment 3. Discussion, they mentioned that b-hydroxypropionic acid can be synthesised from acrylic acid and strong alkali.
I guess that it's some kind od anti-Markovnikov addition of NaOH, for example, and Michael acceptor, acrylic acid.
Is that true or this is some completely different reaction?
3. Methacrylic acid
https://en.wikipedia.org/wiki/Methacrylic_acid
They mentioned 2 reactions that caught my eye - reducing double bond to single bond using amalgam, and complete removal of double bonded carbon by
fusing acid and alkali.
So, this reactions gave me some ideas:
1. Allyl alcohol -> 1,3 propanediol
If reacting acrylic acid and alkali yields b-hydroxypropionic acid, maybe allyl alcohol would yield 1,3 propanediol.
Unless Michael acceptor is necessary for that reaction to work.
What are reaction conditions for such an reaction to occur?
I guess it doesn't involve high temperatures or anhydrous conditions, because in such conditions, b-hydroxypropionic acid would just decompose back
to acrylic acid.
2. Allyl alcohol -> 1-propanol.
This is another use of allyl alcohol I got in mind. Is sodium amalgam reduction of double bonds "universal" or specific to some compounds, like
methacrylic acid?
3. Destroying double bond by fusing with alkalis
This is more of general question - is there a name for reactions like that (methacrylic acid -> propanoic acid)?
Any help is welcome
|