Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: The reaction between a dihalomethane and a hydroxyl/alcohol group
Electra
Hazard to Others
***




Posts: 179
Registered: 11-12-2013
Member Is Offline

Mood: No Mood

[*] posted on 24-1-2014 at 12:58
The reaction between a dihalomethane and a hydroxyl/alcohol group


It is known that catechols or other molecules with two hydroxyl groups in the ortho position on a benzene ring can be deprotanated by a base after which a dihalomethane can react and close the ring. This forms a methylenedioxy group. I also understand that there is a risk of dimer formation if two dihalomethanes connect two of the substrate molecule together.

If a molecule was to be methylenated like this, and there was a hydroxyl group also at the other end of the molecule, brancing from a chain on the other side of the benezene ring, but by itself, would the dihalomethane irreversibly bind to this, leaving the other half of the dihalomethane dangling, or even worse, to chain-connect with the end of another molecule?

I understand that once the methylenedioxy ring is formed, it doesn't easily get deprotanted in the solution. I am not clear about the other aspects. Will a dihalomethane recklessly bind to any deprotanted hydroxyl group in such a reaction?


For instance:

Is this bond able to be formed from R-OH:
R-O-CH2-Br as a side reaction?

If so, can that be cleaved to remove the CH2-Br, or even possibly hydrogenating it to a R-H type situation, seding a CH3-Br into the solution?

Edit:

Answered my own question with some additional research. Feel free to delete this. Apperently a -COOH group would not be effected in a substituion reaction even if deprotanated because the oxygen double bond and oh bond form a sort of resonance stability that is far less reactive than a lone -OH group

[Edited on 24-1-2014 by Electra]
View user's profile View All Posts By User
Nicodem
Super Moderator
Thread Moved
25-1-2014 at 09:33

  Go To Top