What happens when you add a halide in acid to a ketone?

[jirotrom]

Cl2 in H3O+ + Acetone=

Cl2 in H3O+ + Cyclohexanone=

Cl2 in OH- + Acetone=

Cl2 in OH- + Cyclohexanone=


Please help with these reactions I think I have a good idea of what I am missing but I would like an explanation

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[UndergradGuy7]

Cl2 in H3O+ + Acetone=

Cl2 in H3O+ + Cyclohexanone=

Cl2 in OH- + Acetone=

Cl2 in OH- + Cyclohexanone=


Please help with these reactions I think I have a good idea of what I am missing but I would like an explanation

Replace alpha hydrogen with halogen.

Under acidic conditions it would just replace one (according to my book I think), but in destroyer and it has been discussed here a problem said "excess Cl2" so it replaced all alpha hydrogens with Cl.

Under basic conditions it replaces all alpha hydrogens like in acetone it would become CH3(C=O)CX3. It can go further, then another OH- would come and substitute the CX3 making it CH3(C=O)OH...
but since we are under basic conditions the proton gets deprotonated CH3(C=O)O- so we have to add acid to neutralize it. Side product is CHX3. The side product is important in lab tests like the "iodoform test."

See... http://en.wikipedia.org/wiki/Haloform_reaction

For the cyclohexanone it will just replace the alpha hydrogens with Cl under basic conditions. It won't break the ring and make it a carboxylic acid. You can only do that with methyl ketones.

 

[jirotrom]

thanks a bunch!