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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

cis-3,4-Dimethylcyclobutene undergoes thermal ring opening to form the two products shown. One of the products is formed in 99% yield, the other in 1% yield. Which is which?

Explain why two different products are formed from disrotatory ring closure of (2E,4Z,6Z)-octatriene, but only one product is formed from disrotatory ring closure of (2E,4Z,6E)-octatriene.

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b. What would be the product if trans-2-butene were used instead of ethene?

Show how the reactant can be converted to the product in two steps.
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