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Topic: Felkin-Aln-Eisenstein model for cyclic ketones.  (Read 3257 times)

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Offline Markovnikov

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Felkin-Aln-Eisenstein model for cyclic ketones.
« on: November 03, 2009, 04:03:36 PM »
In lab I made a Luche reduction of Pulegone to form cis-pulegol.

I tried to use the Felkin-Aln-Eisenstein model to explain the stereochemistry of the reaction. But as I tried to draw the models neither the boat or the chair (is this the proper names for the two conformations in English? :-X) conformation had the most electronegative group (the CH(CH3)2 group) perpendicular to the C=O pi-system.

Is there another model that should be applied for cyclic ketones? Or are the models not applicable for reductions since the Nu- is a small hydride (H-).

Thank you for any help/comments.
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Offline movies

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Re: Felkin-Aln-Eisenstein model for cyclic ketones.
« Reply #1 on: November 03, 2009, 05:09:58 PM »
The Felkin–Anh–Eisenstein model is for predicting stereochemistry in acyclic systems, so it is really not applicable in this case.
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Offline Markovnikov

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Re: Felkin-Aln-Eisenstein model for cyclic ketones.
« Reply #2 on: November 04, 2009, 01:07:37 AM »
Ah! That's right! Even says in my lecture notes!  :-X

So I guess it's all about sterics then?
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