Question: Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the σ bonds that are broken or formed in each reaction.

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01

Electrocyclic and cycloaddition reactions

A pericyclic reaction (rearrangement) involving the conversion of a pi bond to a sigma bond or vice-versa is referred to as an electrocyclic reaction.

The reaction between two pi bonds of two molecules resulting in a cyclic structure is termed a cycloaddition reaction.

02

Sigmatropic reaction

The sigmatropic reaction involves the cleavage of a sigma σ bond followed by the rearrangement of a pi π bond and the formation of a sigma bond.

03

Classification of the given reactions

a.

Reaction a

The reaction involves the conversion of a sigma bond to a pi bond.

Therefore, it is an electrocyclic reaction.

b.

Reaction b

The reaction involves the conversion of two pi bonds to two sigma bonds, resulting in a cyclic structure.

Therefore, the given reaction is a cycloaddition reaction.

c.

Reaction c

Here, a pi bond gets converted into a sigma bond. Therefore, the given reaction is electrocyclic.

d.

Reaction d

The reaction involves the cleavage of a sigma bond and the migration of a pi bond.

Therefore, it is a sigmatropic rearrangement reaction.

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Most popular questions from this chapter

Question:Using orbital symmetry, explain why a Diels–Alder reaction does not take place under photochemical reaction conditions.

Question: (a) What product is formed when each compound undergoes a thermal electrocyclic ring opening? (b) What product is formed when each compound undergoes a photochemical electrocyclic ring opening?

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: [4 + 2] Cycloadditions with o-quinones such as B are often complex because a variety of products are possible.a. Draw arrows to illustrate how each product is formed when B reacts with styrene, and label the “diene” and “dienophile” components.


b. Draw arrows to illustrate how each product is formed when B reacts with buta-1,3-diene, and label the “diene” and “dienophile” components.


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