Homework 4

Carey, pages 182 - 186 :
Problems 4.19 - 4.46

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1. Given that Kw = [H+] [OH-] = 10-14 , explain why the pKa of H2O is cited as 15.7 and the pKa of H3O+ as -1.7 .

2. The pKa of CH3OH2+ (protonated methanol) is -2.2. Predict the preferred direction of an equilibrium acid-base
reaction between H3O+ and CH3OH.

3. Write a complete mechanism for the SN1 reaction of t-butyl alcohol with HBr.

4. Write a complete mechanism for the SN2 reaction of HI with methanol.