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Chapter 27: Q 56. (page 1104)

Question: Use curved arrows to show how E is converted to F by a two-step reaction sequence consisting of a [1,5] sigmatropic rearrangement followed by a [4 + 2] cycloaddition.

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01

[1,5] sigmatropic rearrangement

It is the shift of a group, mainly hydride, alkyl, or aryl, from C1to C5 carbon in a π-system. This shift can take place in a cyclic as well as in an open-chain structure, hence making this rearrangement more useful.

02

[4 + 2] cycloaddition

It is a pericyclic reaction in which one of the reactants contributes 4 π-electrons to the bonding. At the same time, another reactant contributes 2π-electrons to the bonding giving a six-membered ring.

03

Mechanism of the given reaction

The mechanism of the given reaction is shown hereunder.

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Most popular questions from this chapter

Question: How can X be prepared from a constitutional isomer by a series of [2+2]cycloaddition reactions? Interest in molecules that contain several cyclobutane rings fused together has been fueled by the discovery of pentacycloanammoxic acid methyl ester, a lipid isolated from the membrane of organelles in the bacterium Candidatus Brocadia anammoxidans. The role of this unusual natural product is as yet unknown.

Question: Draw the products of each reaction.

Question:Using the Woodward–Hoffmann rules, predict the stereochemical pathway for each cycloaddition:

(a) a [6 + 4] photochemical reaction;

(b) an [8 + 2] thermal reaction.

Question: Draw the product of each Diels–Alder reaction and indicate the stereochemistry at all stereogenic centers

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.
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