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Why does tertiary haloalkane form alkene in Williamson Synthesis?

Why does tertiary haloalkane form alkene in Williamson Synthesis?

Grade:12

1 Answers

Ravleen Kaur
askIITians Faculty 1452 Points
6 years ago
The Williamson Ether synthesis is an SN2 reaction. Since the SN2 reaction proceeds through a single step where thenucleophile performs a “backside attack” on the alkyl halide. The “big barrier” for the SN2 reaction issteric hindrance.The rate of the SN2 reaction was highest for methyl halides, then primary, then secondary, then tertiary (which essentially don’t happen at all) same trend is followed in this reaction.

One substrate that fails completely with the Williamson is tertiary alkyl halides. This should be no surprise, since a backside attack on a tertiary alkyl halide encounters tremendous steric hindrance. Instead of substitution, elimination reactions occur instead [via E2]. So it forms alkene rather than ether.

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