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
This is the end of the preview. Sign up
access the rest of the document.