Organic Question ~~!

[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/

 

[needzmoar]

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/

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.

 

[Clancyp]

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.

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.

 

[needzmoar]

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.

sure, gimme a second.

 

[needzmoar]

View attachment clancy.gif

 

[Clancyp]

View attachment 17691

thank you so much! i got that far but the Cl on the NH4 was throwing me off. You are a god among men, taken your test yet sir?

 

[needzmoar]

thank you so much! i got that far but the Cl on the NH4 was throwing me off. You are a god among men, taken your test yet sir?

no worries. Yeah, I took it a couple weeks ago and I made sure I didn't eat anything spicy the day before my exam 😛

 

[Clancyp]

no worries. Yeah, I took it a couple weeks ago and I made sure I didn't eat anything spicy the day before my exam 😛

Haha hope that helped. Well let me know if you need anything sir, appreciate the help again. Goodluck with this cycle!