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Chapter 28: Q36P (page 1238)

Propose a mechanism for the following reaction:

Short Answer

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The mechanism of the reaction is given below.

Step by step solution

01

Sigmatropic rearrangement

Sigmatropic reactions fall under the category of pericyclic reactions. The count of pi bonds does not change in this rearrangement. A change is observed in the position of the pi bonds.

These kinds of reactions possess great stereoselectivity.

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02

Predicting the mechanism of the given reaction

The mechanism of the reaction is shown below.

Mechanism of the given reaction

In the first step, the negative charge on N-methylpyridine-N-oxide attacks the carbonyl carbon of acetic anhydride forming the acetate ion.

In the second step, the acetate ion abstracts the hydrogen and forms an alkene group.

In the third step, an intramolecular rearrangement leads to the formation of the desired pyridine-substituted product.

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Most popular questions from this chapter

A student found that heating any one of the isomers shown here resulted in scrambling of the deuterium to all three positions on the five-membered ring. Propose a mechanism to account for this observation.

Show how norbornane can be prepared from cyclopentadiene.

If isomer A is heated to about 100 °C, a mixture of isomers A and B is formed. Explain why there is no trace of isomer C or D.

Draw the product of each of the following sigmatropic rearrangements:

Problem:a. Under thermal conditions, will ring closure of (2E,4Z,6Z,8E)-2,4,6,8-decatetraene be conrotatory or disrotatory?

b. Will the product have the cis or the trans configuration?

c. Under photochemical conditions, will ring closure be conrotatory or disrotatory?

d. Will the product have the cis or the trans configuration?
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