The ratio of elimination to substitution is exactly the same (26% elimination) for 2-bromo- 2-methylbutane and 2-iodo-2-methylbutane in 80% ethanol/20% water at 25°C.
(a) By what mechanism does substitution most likely occur in these compounds under these conditions?
(b) By what mechanism does elimination most likely occur in these compounds under these conditions?
(c) Which substrate undergoes substitution faster?
(d) Which substrate undergoes elimination faster?
(e) What two substitution products are formed from each substrate?
(f) What two elimination products are formed from each substrate?
(g) Why do you suppose the ratio of elimination to substitution is the same for the two substrates?