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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Altered State on October 23, 2013, 07:23:56 PM

Title: Annulation and eliminations
Post by: Altered State on October 23, 2013, 07:23:56 PM
In the top of the img is the reaction, and below is my attempt.

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FH4XJWzo.png&hash=8a4d19c450764eb754d678f81d7ea445)

What am I missing here? How can that ketone be "eliminated" with those conditions?
Title: Re: Annulation and eliminations
Post by: Doc Oc on October 24, 2013, 09:25:52 AM
Is "pent-3-en-2-ona" a typo or is the rest of the word cut off?  That could make a huge difference
Title: Re: Annulation and eliminations
Post by: mst on October 24, 2013, 09:44:16 AM
That's easy, it doesn't  ;)
There is a hydroxy group missing in the target molecule, the ketone is just enolizing to form an aromatic System.
That's a Standard hauser annulation if you want to look it up.
Title: Re: Annulation and eliminations
Post by: Altered State on October 24, 2013, 09:46:00 AM
Is "pent-3-en-2-ona" a typo or is the rest of the word cut off?  That could make a huge difference

Not a typo, it's pent-3-en-2-one in Spanish.
Title: Re: Annulation and eliminations
Post by: Altered State on October 24, 2013, 09:46:41 AM
That's easy, it doesn't  ;)
There is a hydroxy group missing in the target molecule, the ketone is just enolizing to form an aromatic System.
That's a Standard hauser annulation if you want to look it up.

That's what I thought. Thanks.