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Chapter 27: Q 24. (page 1096)

Question: What product is formed from the Claisen rearrangement of each starting material?

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Sigmatropic rearrangement

Sigmatropic rearrangement comes under the category of pericyclic reaction. The pi bonds present in the reactant as well as the product is constant in the case of sigmatropic rearrangement.

02

Claisen rearrangement

Claisen rearrangement comes under the class of [3,3] sigmatropic rearrangement. In this rearrangement reaction, an allyl vinyl ether or allyl aryl ether gets subjected to [3,3] sigmatropic rearrangement.

03

Step 3: Identifying the product is formed from the Claisen rearrangement of each starting material

a. The starting material which is allyl vinyl ether gets subjected to [3,3] sigmatropic rearrangement to form 2-(cyclohex-2-enyl)acetaldehyde. The reaction can be given as:

Product formed by the Claisen rearrangement of compound a

b. The given starting material undergoes [3,3] sigmatropic rearrangement to form 1-allyl cyclohexanecarbaldehyde. The reaction can be given as:

Product formed by the Claisen rearrangement of compound b

c. The given starting material undergoes [3,3] sigmatropic rearrangement to form 2-(1-vinylcyclohexyl)acetaldehyde. The reaction can be given as:

Product formed by the Claisen rearrangement of compound c

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

Question:(a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene?

(b) Does this reaction proceed in a suprafacial or antarafacial manner under

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(c) Does this reaction proceed in a suprafacial or antarafacial manner under

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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.
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