DIR Return Create A Forum - Home
---------------------------------------------------------
Chemistry:The Central Science
HTML https://kolathechemist.createaforum.com
---------------------------------------------------------
*****************************************************
DIR Return to: Organic Laboratory Chemistry
*****************************************************
#Post#: 2013--------------------------------------------------
General Organic Question
DIR By: Michel
Date: January 26, 2013, 9:13 am
---------------------------------------------------------
Using enamine synthesis, how would you transform ethanal to
pentan-2,4-dione?
#Post#: 2653--------------------------------------------------
Re: General Organic Question
DIR By: Marie Curiana
Date: August 4, 2013, 4:58 pm
---------------------------------------------------------
--- Quote from: Michel link ---
>
> Using enamine synthesis, how would you transform ethanal to
pentan-2,4-dione?
>
--- End Quote ---
Here's my suggestion©
Firstly react ethanal with NH(CH3)2, then this will produce
enamine. Then chlorinate the double bond of the enamine formed,
using Cl2, in suitable solvent, after which you can hydrolyse
the dichloro compound so formed to diol using aq KOH. Not sure
how to proceed further though. The vic diol dormed after
hydrolysis can't be oxidized to a dione, so I'd agree Im lost
here! :(
#Post#: 2654--------------------------------------------------
Re: General Organic Question
DIR By: Marie Curiana
Date: August 4, 2013, 5:02 pm
---------------------------------------------------------
OK, its possible to oxidize the vic diol to dione using nitric
acid. the last step now is: elimination of the amino group.
However i'm still generally wary of this procedure!!
#Post#: 2668--------------------------------------------------
Re: General Organic Question
DIR By: Michel
Date: August 5, 2013, 1:07 am
---------------------------------------------------------
--- Quote from: Michel link ---
>
> Using enamine synthesis, how would you transform ethanal to
pentan-2,4-dione?
>
--- End Quote ---
Was sounding a bit plausible until i started thinking of how to
eliminate that bulky NH(CH3)2 group!
*****************************************************
Page 1 of 1