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Topic: Help with reaction!  (Read 3548 times)

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Offline Moz29386

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Help with reaction!
« on: October 25, 2010, 09:59:34 AM »
This is the molecule:

http://www.free-imagehosting.com/show.php/7042_structure.bmp.html

Cis and trans isomer.

One of these isomers reacts with 4Na/4(ch3)3SiCl

the other doesnt. Why?

I think it has something to do with the SN2 and E2 mechanisms

Offline discodermolide

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Re: Help with reaction!
« Reply #1 on: October 25, 2010, 10:05:18 AM »
This is the molecule:

http://www.free-imagehosting.com/show.php/7042_structure.bmp.html

Cis and trans isomer.

One of these isomers reacts with 4Na/4(ch3)3SiCl

the other doesnt. Why?

I think it has something to do with the SN2 and E2 mechanisms
Think about enolisation and the trapping of enols formed in situ with TMSCl
Development Chemists do it on Scale, Research Chemists just do it!
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Offline Moz29386

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Re: Help with reaction!
« Reply #2 on: October 25, 2010, 11:00:23 AM »
This is the molecule:

http://www.free-imagehosting.com/show.php/7042_structure.bmp.html

Cis and trans isomer.

One of these isomers reacts with 4Na/4(ch3)3SiCl

the other doesnt. Why?

I think it has something to do with the SN2 and E2 mechanisms
Think about enolisation and the trapping of enols formed in situ with TMSCl


k...

Offline discodermolide

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Re: Help with reaction!
« Reply #3 on: October 25, 2010, 02:23:43 PM »
What does k... Mean?
You are using Na, a source of electrons, perhaps you generate a radical anion here which is trapped by the tms cl to give the tms enol ether.
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Offline Moz29386

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Re: Help with reaction!
« Reply #4 on: October 25, 2010, 06:28:23 PM »
What does k... Mean?
You are using Na, a source of electrons, perhaps you generate a radical anion here which is trapped by the tms cl to give the tms enol ether.


The product is supposed to be c14 h28 O2 Si2

for the isomer that reacts.

Offline discodermolide

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Re: Help with reaction!
« Reply #5 on: October 25, 2010, 06:34:13 PM »
What does k... Mean?
You are using Na, a source of electrons, perhaps you generate a radical anion here which is trapped by the tms cl to give the tms enol ether.


The product is supposed to be c14 h28 O2 Si2

for the isomer that reacts.
Then make my answer plural
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

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