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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Moz29386 on October 25, 2010, 09:59:34 AM

Title: Help with reaction!
Post by: Moz29386 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

Title: Re: Help with reaction!
Post by: discodermolide on October 25, 2010, 10:05:18 AM

Quote from: Moz29386 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

Think about enolisation and the trapping of enols formed in situ with TMSCl

Title: Re: Help with reaction!
Post by: Moz29386 on October 25, 2010, 11:00:23 AM

Quote from: discodermolide on October 25, 2010, 10:05:18 AM

Quote from: Moz29386 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

Think about enolisation and the trapping of enols formed in situ with TMSCl

k...

Title: Re: Help with reaction!
Post by: discodermolide 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.

Title: Re: Help with reaction!
Post by: Moz29386 on October 25, 2010, 06:28:23 PM

Quote from: discodermolide 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.

The product is supposed to be c14 h28 O2 Si2

for the isomer that reacts.

Title: Re: Help with reaction!
Post by: discodermolide on October 25, 2010, 06:34:13 PM

Quote from: Moz29386 on October 25, 2010, 06:28:23 PM

Quote from: discodermolide 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.

The product is supposed to be c14 h28 O2 Si2

for the isomer that reacts.

Then make my answer plural