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Chapter 27: Q 45. (page 1102)

Question: Draw the product of the [3,3] sigmatropic rearrangement of each compound.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

[3,3] sigmatropic rearrangement

The rearrangement of a 1,5 diene to its 1,5-diene isomer by the cleavage of an existing sigma bond and the formation of a new sigma bond is termed as the [3,3] sigmatropic rearrangement

02

[3,3] sigmatropic rearrangements of the given compounds

The [3,3] sigmatropic rearrangement of compound a is shown below.

[3,3] sigmatropic rearrangement of compound a

The [3,3] sigmatropic rearrangement of compound b is shown below.

[3,3] sigmatropic rearrangement of compound b

The [3,3] sigmatropic rearrangement of compound c is shown below.

[3,3] sigmatropic rearrangement of compound c

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Most popular questions from this chapter

Question: Consider the following electrocyclic ring closure. Does the product form by a conrotatory or disrotatory process? Would this reaction occur under photochemical or thermal conditions?

Question: A solution of 5-methylcyclopenta-1,3-diene rearranges at room temperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products are formed from the starting material by a sigmatropic rearrangement involving a C鈥揌 bond. (b) Explain why 2-methylcyclopenta-1,3-diene is not formed directly from 5-methylcyclopenta-1,3-diene by a [1,3] rearrangement.

Question:Draw the product (including stereochemistry) formed from each pair ofreactants in a thermal [4 + 2] cycloaddition reaction.

Question: What type of cycloaddition occurs in Reaction [1]? Draw the product of a similar process in Reaction [2]. Would you predict that these reactions occur under thermal or photochemical conditions?

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.
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