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Chemistry 8 Online
OpenStudy (anonymous):

what is the product formed when 2-(ethan-1'-ol) cyclohexanone undergoes iodoform test followed by its acidification ? explain.

OpenStudy (joannablackwelder):

I think this will help with the first step. http://www.chemguide.co.uk/organicprops/alcohols/iodoform.html

OpenStudy (joannablackwelder):

Well, first, can you draw the reactant?

OpenStudy (anonymous):

|dw:1407776261274:dw|

OpenStudy (joannablackwelder):

Looks right to me :)

OpenStudy (joannablackwelder):

I think we need to follow the "Summary of the reactions during the triiodomethane (iodoform) reaction" section of the page I pasted.

OpenStudy (anonymous):

thnks ... but actually my doubt is that after oxidation of CH3-CH(OH)- group to ketone , will this rxn undergo its second step that is iodination as i have heard that when the methylene carbon comes in between , no iodoform rxn occurs....

OpenStudy (joannablackwelder):

Hm, I'm not sure. Maybe @abb0t can help?

OpenStudy (joannablackwelder):

I'll look into it more though, in the mean time.

OpenStudy (joannablackwelder):

I was thinking about this some more and I never got a methylene carbon in the iodination part. How did you get that?

OpenStudy (joannablackwelder):

The primary carbon on the ethanol group went from being bonded to an OH and an H to being double bonded to an O. So, it never had 2 Hs.

OpenStudy (joannablackwelder):

And none of the carbons are double bonded except to the Os.

OpenStudy (joannablackwelder):

@lall

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