biostudent101

10+ Year Member
Dec 24, 2008
43
0
Status
Pre-Dental
Hi,

question #138 uses chlorine in acid solution to convert cyclohexanone into 2 chloro-cyclohexanone. correct me if i am wrong, but i think Cl2 should be meta to the carbonyl group?

Thanks

its from the 1 ROAD MAP!
 
May 15, 2009
1,922
3
CA
Status
Dental Student
Hi,

question #138 uses chlorine in acid solution to convert cyclohexanone into 2 chloro-cyclohexanone. correct me if i am wrong, but i think Cl2 should be meta to the carbonyl group?

Thanks

its from the 1 ROAD MAP!
ALPHA hydrogens next to the carbonyl group are highly acidic, and they are replaced with Cl in the above reaction.
 

Kneecoal

10+ Year Member
Mar 2, 2009
870
0
Long Island, NY
Status
Pre-Dental
aha! funny, i asked the exact same question a few days ago! it's cyclohexane, not benzene. with cyclohexane, it'd just remove the alpha hydrogen next to the carbonyl group. if it were benzene, then it'd add meta