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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: [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.


c. o-Quinone C reacts with diene D to form heterocycle E by a process that involves a cycloaddition followed by a [3,3] sigmatropic rearrangement. Use curved arrows to illustrate how this two-step sequence occurs. E is not formed directly from C by a Diels– Alder reaction.

Question: What compound forms geranial (Figure 21.6) by a Cope rearrangement ?

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

Question: Draw the product of each electrocyclic reaction.

a. the thermal electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

b. the photochemical electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

c. the thermal electrocyclic ring-opening of cis-5-ethyl-6-methylcyclohexa-1,3-diene

d. the photochemical electrocyclic ring-opening of trans-5-ethyl-6-methylcyclohexa-1,3- diene

Question: What product is formed when each compound in Problem 27.6 undergoes photochemical 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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