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What happens when the above compound is subjected to DCl in MeOD? As a result of tautomerism, I'd expect at least 7H atoms, two alpha to carbonyl carbon (right side), and five at gamma position (two on one position and three on the other); to be replaced with deuterium.

However, I'm not clear about the mechanism that'd be followed to achieve the same. And at the same time I'm not sure if there will be an 8'th replacement at alpha position to the carbonyl carbon (left side).

I know that the hydrogens on the right alpha position is replaced due to enolization and I think I got the mechanism for this, but the rest is a blank for me at the moment.

If someone could please help provide a detailed mechanism, it'd be really helpful. Thanks a lot.

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  • $\begingroup$ Take a look here. It is under basic conditions but it should serve as guide as long as you know how to form enols in acid. chemistry.stackexchange.com/questions/88672/… $\endgroup$ – user55119 Mar 21 '19 at 12:53
  • $\begingroup$ I do know how they form. It is mostly the deuteration I have problems with since the two books I have about organic chemistry doesn't really cover this subject. But thanks for the help I think I understand how to tackle this now. My only last question would be if there is gonna be 7 or 8 replacements? (as in the original question) $\endgroup$ – Simone Maarup Pedersen Mar 21 '19 at 21:29
  • $\begingroup$ Here are acid and base catalyzed deuterations of a ketone: chem.libretexts.org/Bookshelves/Organic_Chemistry/… enone is simply an extended ketone. Eight maximum! $\endgroup$ – user55119 Mar 21 '19 at 21:47

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