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Chapter 27: Q 55. (page 1103)

Question: Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

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01

Electrocyclic reaction

The reactions that involve the conversion of a pi bond of a conjugated system to a sigma bond or vice-versa are named electrocyclic reactions.

Conjugated systems involving an even number of pi electrons undergo conrotation, while conjugated systems with an odd number of pi electrons undergo disrotation under thermal conditions.

02

Preparation of the given product

The conversion of the starting material to the given product involves two main steps:

  • 8 pi electrocyclic ring-opening (conrotatory) and
  • 6 pi electrocyclic ring-opening (conrotatory).

The reactions are shown below.

Reactions involved in the formation of the product

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Most popular questions from this chapter

Question: a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b) What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.

Question:Draw the product (including stereochemistry) formed from each pair ofreactants in a thermal [4 + 2] cycloaddition reaction.

Question: Heating A results in two successive [3,3] sigmatropic rearrangements鈥擟laisen reaction followed by Cope reaction鈥攖o afford 尾-Sinensal, a component of mandarin orange oil. What is the structure of 尾-sinensal?

Question: Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the 蟽 bonds that are broken or formed in each reaction.

Question: Draw a stepwise, detailed mechanism for the following reaction.
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