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Chapter 27: Q 19. (page 1093)

Question:What type of sigmatropic rearrangement is illustrated in each equation?

Short Answer

Expert verified

Answer

a. [1,3]-D shift

b. [3,3]-Sigmatropic rearrangement

Step by step solution

01

Sigmatropic rearrangement 

Sigmatropic rearrangement is a type of pericyclic reaction that involves the making and breaking of -bonds in a single system. The -bond rearranges and takes a new position.

An example of 3,3-sigmatropic rearrangement is given below:

02

Determination of products

a.

In the given reaction, the C-D bond is the sigma bond that breaks, and a new C-D bond forms at the C-3 position.

b.

The given reaction is an example of [3,3]-sigmatropic rearrangement, and the product is given below:

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Most popular questions from this chapter

Question:What starting materials are needed to synthesize each compound by a thermal [4 + 2] cycloaddition?

Question: What cycloaddition products are formed in each reaction? Indicate the stereochemistry of each product.

Question: When both carbons ortho to the aryl oxygen are not bonded to hydrogen, an allyl aryl ether rearranges to a para-substituted phenol. Draw a stepwise mechanism for the following reaction, which contains two [3,3] sigmatropic rearrangements.

Question:(a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene?

(b) Does this reaction proceed in a suprafacial or antarafacial manner under

thermal conditions?

(c) Does this reaction proceed in a suprafacial or antarafacial manner under

photochemical conditions?

Question: What product is formed when each compound undergoes thermal 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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