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Chapter 27: Q 21. (page 1096)

Question: What product is formed from the Cope or oxy-Cope rearrangement of each starting material?

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Sigmatropic rearrangement reaction

Sigmatropic rearrangement reactions are reactions where the sigma bond is cleaved in the reactant. The pi bonds undergo rearrangement to generate new sigma bonds in the product.

02

Cope rearrangement and oxy Cope rearrangement

The reactant, as well as the product, includes isomeric 1,5-dienes in the case of cope rearrangement. The oxy-cope rearrangement makes use of an unsaturated alcohol.

03

Step 3: Identifying the product formed from the Cope or oxy-Cope rearrangement

a. The given compound gets subjected to [3,3] sigmatropic rearrangement leading to the formation of (E)-methyl 4-methylhepta-2,6-dienoate. The reaction can be given as:

Sigmatropic rearrangement of compound a

b. Compound b undergoes [3,3] sigmatropic rearrangement leading to the formation of cyclopia-1,4-diene. The reaction can be given as:

Sigmatropic rearrangement of compound b

c. Compound c undergoes oxy Cope rearrangement to form (E)-cyclonic-5-enone. The reaction can be given as:

Sigmatropic rearrangement of compound c

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Most popular questions from this chapter

Question: Using the Woodward鈥揌offmann rules in Table 27.4, predict the stereochemistry of each reaction.

a. a [6 + 4] thermal cycloaddition

b. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaene

c. a [4 + 4] photochemical cycloaddition

d. a thermal [5,5] sigmatropic rearrangement

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: 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 formed (including stereochemistry) in each pericyclic reaction.

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.
See all solutions

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