Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: ruler9 on September 01, 2010, 04:09:28 PM

Title: Acid hydrolysis of esters
Post by: ruler9 on September 01, 2010, 04:09:28 PM: Can anyone give me the reference journals on acid hydrolysis of esters (recent) plz...
i tried base hydrolysis, it didn't work.

thanks in advance
Title: Re: Acid hydrolysis of esters
Post by: discodermolide on September 02, 2010, 03:24:40 AM: Quote from: ruler9 on September 01, 2010, 04:09:28 PM
Can anyone give me the reference journals on acid hydrolysis of esters (recent) plz...
i tried base hydrolysis, it didn't work.

thanks in advance
No references, but both methods work very well.
For acidic hydrolysis just dissolve your ester in aqueous HCl and heat it. When the reaction is done make it basic pH 12 with NaOH, extract the organic part of the ester. Re-acidify to pH 1-2 with HCl, and extract the acid, it may even precipitate out on acidification depending on structure. Remove solvent and there is your acid.
Title: Re: Acid hydrolysis of esters
Post by: cundi on September 02, 2010, 07:16:10 AM: Which is the ester that you have?
Title: Re: Acid hydrolysis of esters
Post by: demoninatutu on September 02, 2010, 08:35:27 PM: ruler9, you have to give us more information than that. What hydrolysis are you attempting? What conditions did you use? What do you mean by 'it didn't work'?
Title: Re: Acid hydrolysis of esters
Post by: ruler9 on September 04, 2010, 01:58:21 PM: I have used LiOH/1,4 dioxane and KOH/1,4 dioxane almost went from 2 to 10 equivalents and it didn't work
the compound is an aliphatic ester.
Title: Re: Acid hydrolysis of esters
Post by: discodermolide on September 04, 2010, 02:39:17 PM: Quote from: ruler9 on September 04, 2010, 01:58:21 PM
I have used LiOH/1,4 dioxane and KOH/1,4 dioxane almost went from 2 to 10 equivalents and it didn't work
the compound is an aliphatic ester.
Add water to it
Title: Re: Acid hydrolysis of esters
Post by: ruler9 on September 05, 2010, 12:28:22 PM: i did added LiOH in water.. so do we have to use any dioxane to dissolve ester in the above method u said..
can u just write it brief plz...like how much should be the hcl concentration etc
Title: Re: Acid hydrolysis of esters
Post by: discodermolide on September 05, 2010, 01:37:14 PM: Quote from: ruler9 on September 05, 2010, 12:28:22 PM
i did added LiOH in water.. so do we have to use any dioxane to dissolve ester in the above method u said..
can u just write it brief plz...like how much should be the hcl concentration etc

Depends on the ester and the rest of the molecule, I usually use 37% for the hydrolysis and 37% for the pH adjustment. This way you keep the volumes down.
Title: Re: Acid hydrolysis of esters
Post by: ruler9 on September 08, 2010, 01:02:16 PM: The reaction went well with 10% hcl
@discodermolide :Thanks a ton for helping me.. :) :) :) :) :) :D
Title: Re: Acid hydrolysis of esters
Post by: discodermolide on September 08, 2010, 02:18:30 PM: Quote from: ruler9 on September 08, 2010, 01:02:16 PM
The reaction went well with 10% hcl
@discodermolide :Thanks a ton for helping me.. :) :) :) :) :) :D

My pleasure