SN1 mechanism with tertiary alcohols PDF

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In this reaction we use a SN1 mechanism, therefore there will be 2 steps. Now this is acceptable since we have a tertiary alcohol and forming a carbocation is stable in this sense due to hyper conjugation, we form a stable tertiary tert butyl cation. This happens because we took HBr and put it in water, due to its property as a strong acid it fully dissociated leaving Br- and H3O+. The OH is a difficult leaving group so we take the H3O+ and donate one of it protons to OH making it a better leaving group as H2O. Once that leaves we have the acceptable carbo cation. In the next step Br- is allowed to attach and we have excess H2O that left the original tertiary structure. ! For the possible side reaction... this would happen if we had low concentration of Br- and water. The water would then act as a base and accept a proton from one of the methyl groups of the carbo cation. This would result in an elimination reaction and an alkene along side H3O+. This is unlikely since Br- concentration is abundant and this formation is reversible.! ! ! ! !

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