parham3 Posted October 27, 2011 Report Share Posted October 27, 2011 Organic Chemistry Question HELPPP? The following separate reactions are in the S enantiomer CH3-CH2-CH2-CH-OH-CH3 + SOCl2 = CH3-CH2-CH2-CH-OTs-CH3 + CN(-) = CH3-CH2-CH2-CH-Br-CH3 + CH3OH = CH3-CH2-CH2-CH-OH-CH3 +CH3OTs= PLease indicate which one is the nucleophile, electrophile. The sterochemical outcome (ex.racemic/ inversion). And the products. PLease Help, it would be very helpful Link to comment Share on other sites More sharing options...
bored Posted October 27, 2011 Report Share Posted October 27, 2011 I don't remember the specific details of organic chem. but I think the question is asking you to assume all reactants are in their S form and are reacted with other reactants. for each reaction they wan't you to figure out what happens (is it sn1, sn2 or e1 or e2), and based on that you can figure out the outcome of the product.. A. I know socl2 replaces the OH with a Cl, not sure if it applies here since this is an ether. B. CN- is a strong nucleophile and OTS is a great levaing group so its sn2 = inversion of configuration. C. CH3OH can act as sn2 nucleophile or it can also do the other reactions if the substrate is hindered.. D. as said before, the OTS is the leaving group, so probablly an sn2 reaction and inversion.. Link to comment Share on other sites More sharing options...
nick Posted October 27, 2011 Report Share Posted October 27, 2011 I don't remember the specific details of organic chem. but I think the question is asking you to assume all reactants are in their S form and are reacted with other reactants. for each reaction they wan't you to figure out what happens (is it sn1, sn2 or e1 or e2), and based on that you can figure out the outcome of the product.. A. I know socl2 replaces the OH with a Cl, not sure if it applies here since this is an ether. B. CN- is a strong nucleophile and OTS is a great levaing group so its sn2 = inversion of configuration. C. CH3OH can act as sn2 nucleophile or it can also do the other reactions if the substrate is hindered.. D. as said before, the OTS is the leaving group, so probablly an sn2 reaction and inversion.. A. I think OP meant this to be a secondary alcohol. In that case, SOCl2 is a nucleophile that attacks the carbon that the -OH group is attached to (the electrophile or substrate) in an Sn2 reaction. This reaction is rather sterically hindered (as it is a secondary alcohol) so it will be a fairly slow Sn2 reaction. Link to comment Share on other sites More sharing options...
thatonekid Posted October 28, 2011 Report Share Posted October 28, 2011 Moved to MCAT forum. There's lots of great help here (especially for ochem). Link to comment Share on other sites More sharing options...
IamIDP Posted October 29, 2011 Report Share Posted October 29, 2011 Moved to MCAT forum. There's lots of great help here (especially for ochem). lol no one is responding anymore, you should have kept it where it was.... Link to comment Share on other sites More sharing options...
thatonekid Posted October 30, 2011 Report Share Posted October 30, 2011 lol no one is responding anymore, you should have kept it where it was.... Got to keep things organized. Link to comment Share on other sites More sharing options...
Recommended Posts
Archived
This topic is now archived and is closed to further replies.