orgo dat Q from DAT DESTROYER #138

[biostudent101]

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!

---

Members don't see this ad.

 

[nze82]

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]

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