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Chapter 27: Q 50. (page 1103)

Question: What type of pericyclic reaction is illustrated in each reaction?

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01

Electrocyclic reaction

The pericyclic reactions that involve the conversion of a sigma bond to a pi bond or vice-versa are known as electrocyclic reactions.

02

Sigmatropic rearrangement

The reactions that involve the migration of a sigma bond followed by the delocalization of a pi bond are known as sigmatropic rearrangement reactions.

03

Given reactions

The pericyclic reactions involved in the given reactions are as follows.

Electrocyclic reaction

The given reaction involves the electrocyclic ring-opening.

Sigmatropic rearrangement

The given reaction involves a [1,2] hydrogen shift and, therefore, is a sigmatropic reaction.

Electrocyclic ring closure

The given reaction is an electrocyclic ring-closure reaction.

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Most popular questions from this chapter

Question:Draw a stepwise mechanism for the Carroll rearrangement, a reaction that prepares a纬,未-unsaturated carbonyl compound from a尾-keto ester and allylic alcohol in the presence ofbase.

Question: What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.

Question: The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.

Question: Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

Question: What product is formed when each compound undergoes thermal electrocyclic ring-opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.
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