Destroyer Road Map #1 Help!

[longlashes]

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[PD3]

If that reaction is acid catalyzed, shouldn't it result in 1-hydroxy-1-chlorocyclohexane?

 

[rollredroll]

i think c=o is an activator and will o/p direct.

 

[longlashes]

i think c=o is an activator and will o/p direct.

I thought carbonyls are deactivators?

 

[airsimon]

Its not a benzene ring so o/m/p directing doesn't matter. Anywho if it WAS a benzene group it would direct ortho para because of the lone electrons on the oxygen, which would add to the benzene ring and induce resonance (activator). However if it was a C6H5-C=O then it would be meta directing since there are no lone pairs to help stabalize the resonance structure.

 

[cuttiedentist]

it does that because the hydrogen bonded to carbon next to carbony carbon is the most acidic and its easier to remove that. so Cl substitude that carbon. if it was a benzene ring I believe it would be meta directing
correct me if im wrong

 

[PD3]

it does that because the hydrogen bonded to carbon next to carbony carbon is the most acidic and its easier to remove that. so Cl substitude that carbon. if it was a benzene ring I believe it would be meta directing
correct me if im wrong

What are you saying is pulling off the H? It is an acidic solution. this is what I don't understand. If it was Cl2 in OH-, then that would make sense. Since it's an acidic solution, it seems as though something would be protonated.

 

[hokie4life]

What are you saying is pulling off the H? It is an acidic solution. this is what I don't understand. If it was Cl2 in OH-, then that would make sense. Since it's an acidic solution, it seems as though something would be protonated.

yea this makes sense...hmm i'm confused now too so why does Cl add to that position? since it is acid catalyzed it shoudn't be pylling off an acidic H.

 

[smarterray]

I drew the mechanism out. It is important to realize this reaction is ACID catalyzed, so 1) there are no negative charges allowed in the mechanism and 2) the carbonyl oxygen will be protonated to allow for the enol to form.

P.S. Please correct me if this mechanism is wrong.

 

[smarterray]

Also, like someone said above, this is not benzene you're dealing with, so o/p-direction and whatnot is not important.