D Deepa100 Junior Member 15+ Year Member Joined Aug 24, 2006 Messages 1,027 Reaction score 1 Points 4,531 Jun 15, 2008 #1 Advertisement - Members don't see this ad Hi, Does anyone remember why SN2 works better for reactions of alcohols with HBr when you use PBr3 or SoCl2? I used to know...
Advertisement - Members don't see this ad Hi, Does anyone remember why SN2 works better for reactions of alcohols with HBr when you use PBr3 or SoCl2? I used to know...
T the lost crow Full Member 10+ Year Member 15+ Year Member Joined Feb 17, 2008 Messages 11 Reaction score 0 Points 0 Pre-Medical Jun 15, 2008 #2 The reaction isn't an SN2. It's Sn2-like in terms of stereochemistry. Losing an OH is unstable thus you have to enhance the leaving group. Upvote 0 Downvote
The reaction isn't an SN2. It's Sn2-like in terms of stereochemistry. Losing an OH is unstable thus you have to enhance the leaving group.
1 161927 Jun 15, 2008 #3 HBr is acidic, so if water leaves, carbocation rearrangements can occur. You may end up with the wrong product. No rearrangements are possible with PBr3 and SOCl2 because they are SN2-like. Upvote 0 Downvote
HBr is acidic, so if water leaves, carbocation rearrangements can occur. You may end up with the wrong product. No rearrangements are possible with PBr3 and SOCl2 because they are SN2-like.
D Deepa100 Junior Member 15+ Year Member Joined Aug 24, 2006 Messages 1,027 Reaction score 1 Points 4,531 Jun 16, 2008 #4 DCODY said: HBr is acidic, so if water leaves, carbocation rearrangements can occur. You may end up with the wrong product. No rearrangements are possible with PBr3 and SOCl2 because they are SN2-like. Click to expand... Got it, thanks. Upvote 0 Downvote
DCODY said: HBr is acidic, so if water leaves, carbocation rearrangements can occur. You may end up with the wrong product. No rearrangements are possible with PBr3 and SOCl2 because they are SN2-like. Click to expand... Got it, thanks.
