SN2 inversion of products?

[tnmoonprism]

---

Members don't see this ad.

Hello,
I was wondering if anyone has any insight into when we do an SN2 with a reactant with more than 1 chiral centers, will the products be the inversion of ALL those chiral centers or just the one that was attacked?
Thank you!

 

[Carbohydrates]

To my understanding, just the one that was attacked.

 

[deleted696582]

The product will be an inversion of only the center that was attacked.

 

[tnmoonprism]

Thanks guys!
So that means if the reactant has more than 1 chiral centers, our product will be the DIASTEREOMER and not the enantiomer of the reactant right?

 

[DrNutmeg]

Thanks guys!
So that means if the reactant has more than 1 chiral centers, our product will be the DIASTEREOMER and not the enantiomer of the reactant right?

It's not an isomer at all.

 

[DAT Destroyer]

Hello,
I was wondering if anyone has any insight into when we do an SN2 with a reactant with more than 1 chiral centers, will the products be the inversion of ALL those chiral centers or just the one that was attacked?
Thank you!

Let us do an example......Consider CN- reacting with 2-fluoro-4 iodooctane. The CN- reacts with the Iodine in SN2 fashion,.....and inverts this carbon. Fluorine is a poor leaving group thus will not react. Thus.....we inverted the carbon bearing the iodine....and left the carbon bearing the fluorine alone.

I hope this helps.

Dr. Romano

 

[tnmoonprism]

Let us do an example......Consider CN- reacting with 2-fluoro-4 iodooctane. The CN- reacts with the Iodine in SN2 fashion,.....and inverts this carbon. Fluorine is a poor leaving group thus will not react. Thus.....we inverted the carbon bearing the iodine....and left the carbon bearing the fluorine alone.

I hope this helps.

Dr. Romano

Ohhhhh It finally makes sense! Thank you Dr. Romano!

 

[DAT Destroyer]

Ohhhhh It finally makes sense! Thank you Dr. Romano!

Glad I could help!