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Answers to the Exercises "SN/E Competition"


With sodium ethoxide, virtually only (about 100 %) E2 elimination occurs. By the abstraction of the β proton through the strong base ethoxide early in of reaction, the formation of the carbenium ion is prevented, although this tertiary carbenium ion could otherwise be formed easily. As a result, the treatment of tertiary alkyl halides with strong bases primarily leads to E2 elimination and not to E1 elimination or an SN1 reaction. Due to very strong steric interactions in the trigonal bipyramidal transition state, SN2 reactions with tertiary alkyl halides are almost impossible.

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