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Chapter 27: Q 54. (page 1103)

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

Short Answer

Expert verified

Answer

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Step by step solution

01

Nazarov cyclization

The reaction proceeds in the presence of an acid. A ring-closing reaction takes place between a conjugated enone and an alkene.

02

Cheletropic reactions

Pericyclic reactions that involve the elimination of a small group or chemical entity are called cheletropic reactions.

03

Mechanism of the given reaction

The mechanism of the reaction is given here under.

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Most popular questions from this chapter

Question: What product is formed by the [3,3] sigmatropic rearrangement of each compound?

Question: What product is formed when each compound undergoes a photochemical electrocyclic reaction? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.

Question: What cyclic product is formed when each decatetraene undergoes photochemical electrocyclic ring closure?

Question: The bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R.Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.

Question: a) What is the structure of C, which is formed by oxy-Cope rearrangement of B with NaOEt?

(b) Draw a stepwise mechanism for the conversion of C to the bicyclic alcohol D.
See all solutions

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