UndergroundChemist
Harmless
Posts: 14
Registered: 10-4-2014
Member Is Offline
Mood: No Mood
|
|
Psilocin deprotonation?
Hey.
So here is how I would Deprotonate psilocin's phenol. I just need someone to see if it's correct or not.
So I dissolve Psilocin in ethanol in a 2 necked round bottom flask(RBF) then add a dripping funnel with dilute KOH slowly start it dripping into the
solution of psilocin in ethanol and keep it below 30 celcius with the help of ice. So my theory now is that hydrogen evolves because of the
Deprotonation and leaves the -O with a negative charge resulting in a compound with this structure
Can someone confirm that this would work? (in theory that is)
|
|
|
Nicodem
|
Thread Moved
10-4-2014 at 11:59 |
Metacelsus
International Hazard
Posts: 2539
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
This would produce water, not hydrogen.
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
What would this even be for? Just get a couple pKa values for the protonated groups to see what happens.
|
|
|
UndergroundChemist
Harmless
Posts: 14
Registered: 10-4-2014
Member Is Offline
Mood: No Mood
|
|
Ahaa so only hydrides deprotonates and produce hydrogen gas?
Anyway is the structure correct and will i end up with it in this reaction
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
If you learn about pKa's, you won't need to ask us about the structure, and you could figure out how much base was needed.
|
|
|
UndergroundChemist
Harmless
Posts: 14
Registered: 10-4-2014
Member Is Offline
Mood: No Mood
|
|
I already know how strong base is needed what I don't know is if it will work I'm pretty sure it will work but I would like some confirmation thank
you.
|
|
|
DraconicAcid
International Hazard
Posts: 4334
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Offline
Mood: Semi-victorious.
|
|
Hydroxide should easily deprotonate a phenol.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
Quote: Originally posted by UndergroundChemist  |
I already know how strong base is needed what I don't know is if it will work I'm pretty sure it will work but I would like some confirmation thank
you. |
The pKa of the protonatable groups will tell you what pH is required to deprotonate which group first, which isn't always the stoichiometric amount of
base, depending on base strength and other reactive groups.
|
|
|
aga
Forum Drunkard
Posts: 7030
Registered: 25-3-2014
Member Is Offline
|
|
| Quote: Originally posted by Chemosynthesis |
The pKa of the protonatable groups will tell you what pH is required to deprotonate which group first, which isn't always the stoichiometric amount of
base, depending on base strength and other reactive groups. |
Jeez. I wish i knew what any of that means.
Being a beginner is hard.
Then again, Base, stoichometric and pH were familiar.
[Edited on 17-4-2014 by aga]
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
| Quote: Originally posted by aga |
Jeez. I wish i knew what any of that means.
Being a beginner is hard.
Then again, Base, stoichometric and pH were familiar.
|
It's a pretty simple extension of pH once you figure out where it comes into play.
http://en.wikipedia.org/wiki/Acid_dissociation_constant
I'll try and explain solely because you ask, aga. I try not to be too explicit with schedule I DEA topics, though I am probably one of the most lax
people active on the forum with regard to drugs based solely on my field.
I am going to try not to make a mistake in explaining this, which means I shouldn't post until tomorrow as I'm in the middle of something and just got
back from a day trip out of town, but here goes.
Basically, it factors into some of the molecular stability or reactivity of compounds. You can look at the pKa's of reactants and products and see if
the pKa's increase (more stable) or decrease, which makes it thermodynamically unfavorable. Here we will use it for protonation/deprotonation. When
you have practically protonatable groups, such as the amine or alcohol groups in psilocin, you find the pH of the groups. The pka of the group in
question (a phenol) is ~10. This tells you that you need to go below a solution pH of 10 to fully protonate the phenols in solution. Now check the
amine. It's slightly above this value, and is the pKa you would take into account if you wanted to make a quaternary salt. This means if you get the
pH inbetween the two groups, you can fully and selectively deprotonate the lower pKa species. Anything else is a different equilibria.
These are all temperature and solvent dependent, and can help with explaining isoeletric points, Zwitterions, etc. These become important in
biochemistry and pharmacology.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
