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an inexperienced student adds a solution of catalytic h2so4 and water to the alkene shown below, expecting to produce 1-cyclobutylethan-1-ol.

Respuesta :

The rearrangement produces a more stable tertiary carbocation and the unexpected product.

In the image shown, the substrate is 1-cyclobutylethene. The attack of H2SO4 and water will lead to the conversion of the alkene to an alkanol. Two possible products may be obtained with one being greater than the other.

The unexpected product (Shown in the image attached) is obtained due to rearrangement of the carbocation intermediate. The rearrangement produces a more stable tertiary carbocation and the unexpected product.

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