Chem 334 - Summer 1998 - Organic Chemistry I
Dr. Carl C. Wamser Dr. Carl C. WamserVollhardt & Schore, pp 201 -205
Problems 1 , 2 , 8 , 9 , 10 , 11 , 12 , 13 , 15 , 17 , 18 , 21
, 22
1. Arrange the following in order of nucleophilicity:
all the halide anions, OH- , H2O , HS-
2. Arrange the same compounds as in problem 1 with respect to their leaving group ability.
3. Arrange the following alkyl halides in order of their reactivity in an SN2 reaction:
bromomethane, 1-bromopropane, 2-bromopropane, chlorocyclohexane
4. Illustrate the mechanism of the SN2 reaction between trans-1-bromo-4-methyl-cyclohexane and CN-, specifically showing the stereochemistry of the reactants and the products.
How would the products differ if the starting material was optically active 1-bromo-4-methylcyclohexane?
5. Write a complete mechanism for the SN2 cleavage of dimethyl ether (CH3OCH3) using concentrated HI.