Hemichordate

Peds
10+ Year Member
May 5, 2008
1,091
4
Status
Resident [Any Field]
If you have a ketone and an aldehyde undergoing aldol condensation, how do you determine which hydrogen gets abstracted by the base in the first step? Is it a hydrogen from the ketone or aldehyde?
 

G1SG2

10+ Year Member
5+ Year Member
May 2, 2008
1,454
2
Status
Pre-Medical
If you have a ketone and an aldehyde undergoing aldol condensation, how do you determine which hydrogen gets abstracted by the base in the first step? Is it a hydrogen from the ketone or aldehyde?
Take a look at what's on the alpha carbon, and the molecule in general. If you have electron withdrawing groups on either the aldehyde or ketone, then that's good because they will stabilize the negative charge on the enolate ion once the alpha hydrogen comes off. Aldehydes are generally more acidic than ketones because the ketone has more electron donating alkyl groups destabilizing the conjugate base, but just look at what's on the molecule, and whether or not there are electron withdrawing groups.
 

loveoforganic

-Account Deactivated-
10+ Year Member
Jan 30, 2009
4,222
12
Status
If you have a similar aldehdye and ketone, you're going to get a mixture of products.
 

boaz

shanah alef
10+ Year Member
7+ Year Member
Dec 31, 2007
1,373
25
bachelor pad
Status
Medical Student
Another very important consideration is what kind of base is used. If it's a big fat bulky base, like LDA or t-BuOK, then the less hindered proton will be abstracted.