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Please help with mechanism (base-catalyzed isomerization of aldol)
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Topic: Please help with mechanism (base-catalyzed isomerization of aldol) (Read 2040 times)
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mirracle4
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Please help with mechanism (base-catalyzed isomerization of aldol)
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April 26, 2015, 12:53:02 AM »
I have to draw a mechanism for this "base-catalyzed isomerization" but I cannot figure out how to start. I don't think the carbon that the hydroxyl group is attached to gets deprotonated since a hydroxyl group is electron donating. I also don't think the alcohol gets deprotonated by the hydroxyl ion. Can someone please help me out with this one?
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orgopete
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Re: Please help with mechanism (base-catalyzed isomerization of aldol)
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Reply #1 on:
April 26, 2015, 02:18:25 AM »
Hint: a carbonyl group is electron withdrawing and can increase the acidity of alpha hydrogens.
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pgk
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Re: Please help with mechanism (base-catalyzed isomerization of aldol)
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April 26, 2015, 06:29:02 AM »
Try to draw the mechanism of the inverse reaction and then, get back. It might be helpful.
Which reaction is more favorable (more stable product) and why?
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mirracle4
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Re: Please help with mechanism (base-catalyzed isomerization of aldol)
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Reply #3 on:
April 26, 2015, 06:08:13 PM »
Ok I think I got it... And I know that the reaction as written forms the more stable product, but is this because the pi bond is more substituted in this product? Is that the only reason?
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Last Edit: April 26, 2015, 06:31:22 PM by mirracle4
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pgk
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Re: Please help with mechanism (base-catalyzed isomerization of aldol)
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April 27, 2015, 11:06:26 AM »
Which one is more conjugated and why?
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Please help with mechanism (base-catalyzed isomerization of aldol)