Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: a confused chiral girl on June 13, 2007, 08:37:47 PM

Title: Separating aldol
Post by: a confused chiral girl on June 13, 2007, 08:37:47 PM

Hi,

I'm wondering if anyone could please draw how this structure would look like after it's separated into the carbonyl electrophile and enolate nucleophile.

thanks!

Title: Re: Separating aldol
Post by: Fry on June 13, 2007, 11:24:41 PM

2,3-dioxobutane with itself?


http://chemfinder.cambridgesoft.com/ChemIndex/ChemIndex/ChemIndex_action.asp?formgroup=base_form_group&dbname=ChemIndex&dataaction=Get_structure&Table=MolTable&Field=MOL_ID&DisplayType=sizedgif&width=225&height=200&StrucID=3976

Title: Re: Separating aldol
Post by: Custos on June 14, 2007, 02:11:14 AM

As a general rule of thumb to go backwards from an aldol condensation look for the beta-keto alcohol, and push the electrons as shown - the proton falling off, tha alcohol becomes the carbonyl electrophile and the resulting anion is stabilized by an adjacent carbonyl.