W wifi08 Full Member 10+ Year Member 15+ Year Member Joined May 14, 2008 Messages 86 Reaction score 3 Points 4,551 Pre-Health (Field Undecided) Aug 4, 2008 #1 Advertisement - Members don't see this ad which yeilds a more stable carbocation/radical 1)H2C=CH+ vinylic 2)H2C=CH-CH2+ allylic 3) +methylcyclohexane i.e. a primary carbon also, which is least reactive towards SN2? CH3CH2CH2I CH3CH2CH2BR
Advertisement - Members don't see this ad which yeilds a more stable carbocation/radical 1)H2C=CH+ vinylic 2)H2C=CH-CH2+ allylic 3) +methylcyclohexane i.e. a primary carbon also, which is least reactive towards SN2? CH3CH2CH2I CH3CH2CH2BR
klutzy1987 StudyingSucks Letsgo Mets 10+ Year Member 15+ Year Member Joined Jan 28, 2008 Messages 2,134 Reaction score 3 Points 4,591 Location New York Dental Student Aug 4, 2008 #2 wifi08 said: which yeilds a more stable carbocation/radical 1)H2C=CH+ vinylic 2)H2C=CH-CH2+ allylic 3) +methylcyclohexane i.e. a primary carbon also, which is least reactive towards SN2? CH3CH2CH2I CH3CH2CH2BR Click to expand... The allyl is resonance stabilized and therefore is the more stable carbocation. I is a much better leaving group than Br and therefore will be much more reactive towards Sn2 reaction than Br. Upvote 0 Downvote
wifi08 said: which yeilds a more stable carbocation/radical 1)H2C=CH+ vinylic 2)H2C=CH-CH2+ allylic 3) +methylcyclohexane i.e. a primary carbon also, which is least reactive towards SN2? CH3CH2CH2I CH3CH2CH2BR Click to expand... The allyl is resonance stabilized and therefore is the more stable carbocation. I is a much better leaving group than Br and therefore will be much more reactive towards Sn2 reaction than Br.
W wifi08 Full Member 10+ Year Member 15+ Year Member Joined May 14, 2008 Messages 86 Reaction score 3 Points 4,551 Pre-Health (Field Undecided) Aug 4, 2008 #3 but what about vinylic vs the primary carbon which will yield more stable carbocation? Upvote 0 Downvote
C chemtex2008 Full Member 10+ Year Member 15+ Year Member Joined Aug 18, 2007 Messages 29 Reaction score 0 Points 0 Dental Student Aug 4, 2008 #4 Primary carbocations are the worst!!! You never see this happen in chemistry (except in very high energy situations such as with mass spec). Upvote 0 Downvote
Primary carbocations are the worst!!! You never see this happen in chemistry (except in very high energy situations such as with mass spec).
doc3232 Full Member 10+ Year Member 15+ Year Member Joined Feb 15, 2008 Messages 3,809 Reaction score 10 Points 4,601 Dental Student Aug 4, 2008 #5 klutzy1987 said: The allyl is resonance stabilized and therefore is the more stable carbocation. I is a much better leaving group than Br and therefore will be much more reactive towards Sn2 reaction than Br. Click to expand... Not that much more reactive, but ya as he said. Br is a very good leaving group. Upvote 0 Downvote
klutzy1987 said: The allyl is resonance stabilized and therefore is the more stable carbocation. I is a much better leaving group than Br and therefore will be much more reactive towards Sn2 reaction than Br. Click to expand... Not that much more reactive, but ya as he said. Br is a very good leaving group.