Treating 1-butanol with sulfuric acid establishes an equilibrium with 1-butyl bisulfate and water as shown.CH3(CH2)2CH2OH + H2SO4 —-> CH3(CH2)2CH2OSO3H + H2Oa. Using curved arrows to symbolize the flow of electrons, propose a mechanism for the conversion of 1-butanol to 1-butyl bisulfate. b. 1-Butyl bisulfate may serve as the precursor to an ether and an alkene, as well as the desired 1-bromobutane.
i. Provide the structures expected for the ether and the alkene that might be produced from 1-butyl bisulfate.
ii. Using curved arrows to symbolize the flow of electrons, provide reaction mechanisms for the formation of each of these by-products and specify whether the mechanisms you write are SN1, SN2, E1, E2, or none of these.
iii. Explain why you would expect bisulfate to be a good leaving group for substitution or elimination reactions.