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Topic: isomerization of fat under basic conditions  (Read 4647 times)

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briteyellowness

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isomerization of fat under basic conditions
« on: August 14, 2005, 10:49:19 AM »
so, how does this happen?  i've been told that a fatty acid salt can be unsaturated, and then it can isomerize.  but i don't understand how it can isomerize under the conditions: NaOH and temp> 100 C,  thanks!
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Re:isomerization of fat under basic conditions
« Reply #1 on: August 14, 2005, 12:15:50 PM »
What can happen if you deprotonate the allylic carbon in an alkene?  What can the intermediate do before reprotonation?
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briteyellowness

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Re:isomerization of fat under basic conditions
« Reply #2 on: August 14, 2005, 03:45:16 PM »
oh, i see, so the double bond can kind of shift over after deprotonation and then its' a different molecule?  the way i was thinking was going from a cis to a trans bond.  is there anyway that is able to happen?
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Re:isomerization of fat under basic conditions
« Reply #3 on: August 14, 2005, 04:55:21 PM »
Yeah, you could get either alkene migration or cis/trans isomerization through essentially the same mechanism.  Whether you get migration or not just depends on which end of the allylic system gets protonated.
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