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explain why eather is the major product in the reaction of tert butylbromide with ethanol


Lilly 22nd Aug, 2022
Answer (1)
rajeevanand843 2nd Sep, 2022

Hello lilly

The major product forms from SN1 ; the alkyl bromide is tertiary, so it is bulky/sterically-hindered , and is more likely to lose Br− as a leaving group before managing to get attacked by a nucleophile (ethanol). The proton on the attached ethanol then dissociates on its own.

That is characteristic of a first -order process, where the slow step is the departure of the leaving group and a carbocation intermediate forms (here, a tertiary carbocation).

There is a minor product from E1 , but this is very minor unless the temperature is sufficiently high. This would be a β elimination, i.e. the alcohol extracts a proton from the carbon adjacent to Br and patches up the carbocation intermediate.

Thank you

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