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Topic: Carbonyl to Imine - cis or trans?  (Read 1736 times)

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Offline maverick1996

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Carbonyl to Imine - cis or trans?
« on: April 21, 2016, 09:46:31 AM »
Heyy!!

So I am reacting an aldehyde/ketone with a primary amine and for this example lets say I have Et-COH and reacting it with PhNH2 (forming PhN=CHEt), how would I know which product is formed? Cis or trans imine?

Has it got to do with the steric repulsion and that the trans isomer is therefore preferred?

Thank youuu

Offline Dan

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Re: Carbonyl to Imine - cis or trans?
« Reply #1 on: April 22, 2016, 02:40:59 AM »
Has it got to do with the steric repulsion and that the trans isomer is therefore preferred?

Generally yes. Imine formation under most standard conditions is reversible, leading to the more thermodynamically stable product.
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Offline maverick1996

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Re: Carbonyl to Imine - cis or trans?
« Reply #2 on: April 25, 2016, 03:26:41 AM »
Thank you

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