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Topic: Reactivity of lactones to nucleophiles?  (Read 1738 times)

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Offline greentea11

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Reactivity of lactones to nucleophiles?
« on: February 01, 2014, 10:12:00 AM »
how do they differ in their reactions to nucleophiles and why?

from the photo i'm comparing the 4 membered ring and the 6 membered ring, so the 2nd and 4th in the photo

Is it to do with the strain of the ring, hence 4 member ring is more strained so less stable, more reactive to nucleophiles?

any help appreciated

Offline discodermolide

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Re: Reactivity of lactones to nucleophiles?
« Reply #1 on: February 01, 2014, 10:14:50 AM »
Yes, the beta-lactone is more reactive. Just look at what is does to the bond angles of the poor carbon atoms, the alpha lactone is even worse!
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