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S N 1 MECHANISM: UNIMOLECULAR SUBSTITUTION - 3° > 2° and no 1° - carbocation intermediate - RDS = formation of carbocation - rearrangement hydrogen shifts AND alkyl shifts possible! - base strength is unimportant - good leaving group (halide of tosylate) - Because the mechanism goes through a carbocation , the leaving group must be attached to either a 3° or 2° carbon to stabilize the intermediate . A methyl or primary leaving group will not form a carbocation. - Since it goes through a carbocation intermediate, there are possibilities for alkyl and hydrogen rearrangements. In mechanism problems, if you see a change in the carbon skeleton between the reactant and the product, automatically suspect a carbocation
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