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Chapter 27: Q 49. (page 1102)

Question: Draw structures for A, B, and C in the following reaction sequence and identify the process that converts B to C.

Short Answer

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Answer

Step by step solution

01

Claisen rearrangement

The [3,3] sigmatropic rearrangement reaction that involves the conversion of an allyl vinyl ether to an unsaturated carbonyl compound is named the Claisen rearrangement.

02

Example of a Claisen rearrangement reaction

A Claisen rearrangement reaction is shown below

03

Given reaction

The products formed in the given reaction are as follows.

Reaction sequence

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Most popular questions from this chapter

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

thermal conditions?

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

photochemical conditions?

Question: What type of sigmatropic rearrangement is illustrated in each reaction?

Question: What cycloaddition products are formed in each reaction? Indicate the stereochemistry of each product.

Question: One step in the synthesis of periplanone B, the chapter-opening molecule, involved anionic oxy-Cope rearrangement of the following unsaturated alcohol. Draw the product that results after protonation of the intermediate enolate.

Question: A solution of 5-methylcyclopenta-1,3-diene rearranges at room temperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products are formed from the starting material by a sigmatropic rearrangement involving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene is not formed directly from 5-methylcyclopenta-1,3-diene by a [1,3] rearrangement.
See all solutions

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