Chem 334 - Summer 1998 - Organic Chemistry I
Dr. Carl C. Wamser Dr. Carl C. WamserVollhardt & Schore, pp 230 -237
Problems 1 , 3 , 4a , 5 , 6 , 7 , 10 , 11 , 12 , 13 , 14 ,
18 , 19 , 22
1. Write a complete mechanism for the conversion of (1R,3S)-1-bromo-1,3-dimethyl-cyclohexane to a mixture of SN1 and E1 products by heating in methanol solvent.
Show all possible products, including their stereochemistry.
2. The fact that a leaving group can also act as a nucleophile leads to what is called the "common ion effect". For example, when NaBr is added to the solvolysis of tert-butyl bromide, the reaction rate is slightly decreased. Explain this with a complete mechanism. Derive a revised rate law that explains the rate decrease quantitatively.