What is the reason for the difference in reactivity observed for #"tertiary butyl bromide"#?

1 Answer
anor277
Dec 4, 2017

Well #"tert-butyl bromide"# likely reacts thru the intermediacy of a #"tert-butyl cation...."#

Explanation:

And so we can represent the process as....

#(i)# #(H_3C)_3C-Brstackrel("slow")rarr(H_3C)_3C^(+) + Br^-#

#(iia)# #(H_3C)_3C^(+) +HO^(-)stackrel("fast")rarr(H_3C)_3COH#...#"substitution"#

#(iib)# #(H_3C)_3C^(+) +HO^(-)stackrel("fast")rarrunderbrace((H_3C)_2C=CH_2)_"isobutylene"+H_2O#...#"elimination"#

Given appropriate conditions, the which must be established by experiment, you could probably tweak the reaction to give mainly substitution, or mainly elimination.

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