Chem 334 - Fall 2001
Organic Chemistry I
Dr. Carl C. Wamser
Carey, pages 163 - 166:
Problems 4.21 - 24, 27 - 40
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.