The sec-butyl cation can react as both a Brnsted-Lowry

Chapter 4, Problem 4.35

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The sec-butyl cation can react as both a Brnsted-Lowry acid (a proton donor) and a Lewis acid (an electron pair acceptor) in the presence of a watersulfuric acid mixture. In each case, however, the product is different. The two reactions are CH3 CH2 sec-Butyl cation CH3 CH3 O HH (1) CH 1 1 1 H2O C CH3 CH H2 CH3 CH2 sec-Butyl cation CH CH3 1 CH3 1 H3O1 (2) 1 H2O C CH3 CH H (a) In which reaction(s) does this cation react as a Lewis acid? In which does it react as a Brnsted-Lowry acid? (b) Write Lewis structures for reactants and products, and show by the use of curved arrows how each reaction occurs.

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