SN2 Ring reaction concept (Need Help)

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

RSD2014

Full Member
10+ Year Member
Joined
Sep 2, 2009
Messages
202
Reaction score
0
Hey guys, I need some clarification on SN2 Ring reaction concept.
Any help would be appreciated.

My understanding of SN2 is that the product is an inversion.
If R ---> then S product.

With a Ring, does the inversion only occur at the Leaving Group position?
What if you have a substituent in Equatorial position, does it go into Axial position in the product?


Cyclohexanesn2rxnA.jpg



Cyclohexanesn2rxnB.jpg






BICYCLO SN2 RXN (Is this correct?)

BicycloSN2rxn.jpg



Which of these is correct? TOP Cyclohexane RXN? BOTTOM Cyclohexane RXN? Is it the same with Bicyclo compound SN2 rxn?
 
in SN2 we use a polar aprotic solvent and we prefer a primary halide....i.e. Rate=K[halide][nucleophile].........That being said we have an inversion of a chiral center ONLY at the reaction site that being where the halide is located. So if something is R-it will become S and vice versa. Both those images seem to be correct......I hope this helps and we can wait in on the others to help.
 
Last edited:
the second cyclohexane substituted(the one with DMSO) product is actually a trans conformation, I believe it is more stable than then first one and third one. correct me please.
 
the second cyclohexane substituted(the one with DMSO) product is actually a trans conformation, I believe it is more stable than then first one and third one. correct me please.


I thought Bulky substituent should be in Equatorial to have a more stable product(?) The second cyclohexane has Bulky group in Axial. Correct me if I'm wrong(?)
 
The 1st drawing is right. when SN2 happens, the back side attack causes an only on the carbon with the cl on it and it doesnt affect the carbon with the 3` carbon. So the carbon with the Cl changes from axil to equatorial. the large group tends to stay on equatorial.
 
Top