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Topic: inter and intra molecular dehydration  (Read 6649 times)

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Offline Doom91

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inter and intra molecular dehydration
« on: February 23, 2009, 01:22:57 AM »
what conditions would favour the intramolecular dehydration of diols and what condition would favour the intermolecular dehydration of the diols if the catalyst is the same sulphuric acid catalyst

Offline azmanam

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Re: inter and intra molecular dehydration
« Reply #1 on: February 23, 2009, 06:43:46 AM »
what products would the intramolecular dehydration of a diol give?
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Offline Doom91

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Re: inter and intra molecular dehydration
« Reply #2 on: February 24, 2009, 02:10:42 AM »
cyclic ether

Offline azmanam

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Re: inter and intra molecular dehydration
« Reply #3 on: February 24, 2009, 06:35:33 AM »
potential ring size and overall concentration will be 2 big determining factors
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Offline Doom91

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Re: inter and intra molecular dehydration
« Reply #4 on: February 24, 2009, 07:53:50 AM »
you mean no of carbons in the ring and the amount of ring strain within the ring ,by the way how does the conc affect the type of minor and major product being formed

Offline azmanam

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Re: inter and intra molecular dehydration
« Reply #5 on: February 24, 2009, 09:39:54 AM »
yes.  number of carbons and ring strain will favor intramolecular dehydration - which ring sizes do you think will be favored?

how do you think con'c will effect inter vs intra?  imagine you had a diol as a neat (read: solventless) liquid, and a diol that was 0.0000001 molar in an inert solvent.  Add catalytic acid to both.  which will give intermolecular product preferentially and which will give intramolecular product preferentially?
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Offline Doom91

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Re: inter and intra molecular dehydration
« Reply #6 on: March 02, 2009, 01:25:47 AM »
 5 or 6 membered ring would be most favourable , smaller deviations from the 109.5degrees for sp3 carbons

Offline azmanam

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Re: inter and intra molecular dehydration
« Reply #7 on: March 02, 2009, 07:52:40 AM »
yes.  (and, actually, 3 membered rings close very fast, as well).
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Offline sanderol

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Re: inter and intra molecular dehydration
« Reply #8 on: March 02, 2009, 01:00:40 PM »
consider entropy!! Entropy would prefer intramolecular.

Offline Doom91

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Re: inter and intra molecular dehydration
« Reply #9 on: March 03, 2009, 01:14:41 AM »
I thought 3 membered ring has quite a great amount of ring strain , great deviation from 109.5(abt 49.5), Therefore unstable . why does it form

Offline azmanam

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Re: inter and intra molecular dehydration
« Reply #10 on: March 03, 2009, 07:43:39 AM »
because its fast.  The orbitals essentially overlap already.  epoxides can be quite stable and isolated.
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