Guest ikaj Posted August 5, 2004 Report Share Posted August 5, 2004 Hi, why is an Iodine ion a better leaving group than an ammonium ion for an SN1 reaction for the formation of a carbocation? thnks Link to comment Share on other sites More sharing options...
Guest hash Posted August 5, 2004 Report Share Posted August 5, 2004 I think its because it has a stronger conjugate acid. ie: HI > NH3 Edit:... actually... I'm somehow doubting that explanation. I don't know why. B'coz ammonium itself is the conjugate acid... hmmm.... anybody else. Link to comment Share on other sites More sharing options...
Guest seonagh Posted August 7, 2004 Report Share Posted August 7, 2004 Hello, The strength of Iodine as a base along with it's size and electron withdrawing ability make it such a good leaving group. All halides have the electron withdrawing thing going for them but the size of Iodine means it can stabilize a charge better during the transition (hence I is better than F). As for the difference b/w Iodine and ammonium, ammonium is a weak base whereas Iodine is a strong base, this I think would be the key feature here that makes the difference overiding the others. Seonagh Link to comment Share on other sites More sharing options...
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