Dehydration of secondary and tertiary alcohols fails to yield ethers, as elimination competes over substitution. Consequently, alkenes are easily formed, and the reaction follows an SN₁ pathway, a concept elaborated upon in higher classes.
Why is the dehydration of secondary and tertiary alcohols unsuccessful in producing ethers, and what competing reactions occur, making alkenes the dominant products?
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The dehydration of secondary and tertiary alcohols to form ethers is generally unsuccessful due to competing elimination reactions. In these cases, the E1 and E2 mechanisms are favored over the SN2 mechanism required for ether formation. The stability of the resulting carbocation intermediates in these elimination reactions is a key factor. Secondary and tertiary carbocations are more stable than primary ones, promoting the elimination of a proton and the formation of alkenes. As a result, in the dehydration of secondary and tertiary alcohols, alkenes become the dominant products, making the synthesis of ethers less favorable under these conditions.