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Chapter 31: Question 31.40 (page 1256)

Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

Answer

The mechanism of the reaction

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Step by step solution

01

About the given reaction

The given starting material consists of a five-membered cyclic ring, double bonds, and a triple bond. It is treated with an acid that gives rise to a network of cyclic rings.

02

About the mechanism of the reaction

The given compound is rearranged and is treated with H3O+that will result in the formation of a species in which the oxygen atom has a positive charge. This species is rearranged, which gives rise to a resonance structure.

03

About the mechanism

The obtained cation is rearranged and treated with water. The process is repeated several times, resulting in the formation of the final product. The overall mechanism is shown below.

Mechanism of the reaction

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  1. H2O,H+
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  3. H2(1 equiv), Pd-C→C
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