The ratio of elimination to substitution is exactly the same (26% elimination) f

Question

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 degrees 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 ration of elimination to substitution is the same for the two substrates?

Explanation / Answer

1) Mostly SN1 MECHANISM is favourable.

2) E1 mechanism

3) 2-iodo-2-methylbutane

4)2-bromo-2-methylbutane

5) 2- methyl butanol-2 .

6) 2- methyl 2- butene , 2-methyl 1-butene.

7) because in both cases intermediate is tertiary carbocation which is more stable.

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