Orgo rxn from destroyer roadmap

[Albuterol]

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hey guys id do a search but im kinda low on time and wanna go to sleep soon haha...but can someone explain this to me..why the Cl is in the ortho position to the ketone.

this is from RM #1..the reaction starts at the start point and goes towards the left reactants...

cyclohexanol + KMnO4, OH-/H3O+ ---->cyclohexanone + Cl2/H3O+--->2-cholorocyclohexanone.

why did it attack the carbon next to the carbonyl group? is it because it ripped the alpha-H...shouldnt the otherside be attacked too? thanks for the hlep..im really clueless on this.

 

[utdent20]

my quick look on it is that.. 0 is activator, its in the list of the all the OH, CH3, NH2, C, C, N, O are a part of it.. including =0 thus.. its ortho. that is why I think!! anyone agree?

 

[funktion]

activator/deactivator groups are only involved in additions to aromatics such as benzene. cyclohexane is not aromatic so this reaction is due to acidity of hydrogens attached to carbon alpha to ketone carbon. Proton is abstracted and resonance stabilized then electrons attack Cl2 for the substitution. it is also possible that the other alpha carbon could also be attacked.

 

[Albuterol]

hmm so if it was Excess Cl2 then the other alpha carbon would be ripped off also right?

btw utdent im pretty sure the c=o is a deactivator and will withdraw electrons and contribute to acidity, and promote the meta position.

 

[klutzy1987]

A double bonded O i neither an activator nor a deactivator, it is imposible to have it on a benzene, It would make too many bonds. If you added Cl2 excess, yes it could completely substitute and make 4 Cl.

 

[Albuterol]

yea i meant its a deactivator on a benzene haha shouldve written that in there..
thanks for the clarification on cl2 excess klutzy

 

[klutzy1987]

It is jimpossible to have a oxo on a benzene, unless you are referring to a carbon and attached to that is the double bonded O, which is a deactivator.

 

[Albuterol]

No i know that u cant have a oxo group on a benzene, i was referring to the second situation u said. sorry man its still early haha

 

[utdent20]

How would an excess of Cl lead to 4 Cl, i thoughtthere would only be 2 even after excess Cl2, they would go on both sides of the =O? can you help Klutzy!

 

[klutzy1987]

How would an excess of Cl lead to 4 Cl, i thoughtthere would only be 2 even after excess Cl2, they would go on both sides of the =O? can you help Klutzy!

Because each alpha carbon has 2 alpha hydrogens. If all of these are replaced that makes 4 alpha hydrogens replaced.