Organic Question ~~!

Started by Clancyp
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Clancyp

Clancyp

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Hey guys! Ive already taken the DAT and taking Ochem 2 right now and have a question about this equation. I have recreate this reaction using arrows, and I understand it, in that the SCH3 attacks the least substituted side (because its in basic solution DMF(?)). But what is the NH4Cl do... or is that the basic solution and DMF just goes with NaSCH3?

http://imageshack.us/photo/my-images/64/photofdx.jpg/
 
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Clancyp said:
Hey guys! Ive already taken the DAT and taking Ochem 2 right now and have a question about this equation. I have recreate this reaction using arrows, and I understand it, in that the SCH3 attacks the least substituted side (because its in basic solution DMF(?)). But what is the NH4Cl do... or is that the basic solution and DMF just goes with NaSCH3?

http://imageshack.us/photo/my-images/64/photofdx.jpg/
Click to expand...

Clancy, SCH3- does not attack the least substituted carbon because of the solvent but because that particular substrate/nucleophile combo favors the SN2 product. The solvent facilitates the reaction because it's aprotic. The NH4Cl salt serves as a proton source to protonate the intermediate.
 
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needzmoar said:
Clancy, SCH3- does not attack the least substituted carbon because of the solvent but because that particular substrate/nucleophile combo favors the SN2 product. The solvent facilitates the reaction because it's aprotic. The NH4Cl salt serves as a proton source to protonate the intermediate.
Click to expand...

I hate to ask this, but do you mind drawing that out and taking a picture of it? Im a little confused, haha thankfully I wasnt presented one of these on the test. I assumed this was just a simple peroxide in base or in acid quesiton.
 
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