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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: What product is formed by [3,3] sigmatropic rearrangement of the following compound? Clearly indicate the stereochemistry around all tetrahedral stereogenic centers.

Question: For each molecular orbital in Figure 27.2, count the number of bonding interactions (interactions between adjacent orbitals of similar phase) and the number of nodes. (a) How do these two values compare for a bonding molecular orbital? (b) How do these two values compare for an antibonding molecular orbital?

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

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 of each Diels鈥揂lder reaction and indicate the stereochemistry at all stereogenic centers
See all solutions

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