of When heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen rearrangement, a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state. Draw the structure of the expected product when this compound undergoes a Claisen rearrangement. • You do not have to consider stereochemistry. For the purposes of this problem, assume that double bonds in an aromatic ring are localized at the positions indicated in the figure. • Include isomerization to a phenol IF appropriate.

of When heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen rearrangement, a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state. Draw the structure of the expected product when this compound undergoes a Claisen rearrangement. • You do not have to consider stereochemistry. For the purposes of this problem, assume that double bonds in an aromatic ring are localized at the positions indicated in the figure. • Include isomerization to a phenol IF appropriate.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

### Claisen Rearrangement of Allyl Aryl Ethers

**Description:**

When heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a **Claisen rearrangement**, which is a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state.

**Task:**

Draw the structure of the expected product when this compound undergoes a Claisen rearrangement.

**Guidelines:**

- You do not have to consider stereochemistry.
- For the purposes of this problem, assume that double bonds in an aromatic ring are localized at the positions indicated in the figure.
- Include isomerization to a phenol if appropriate.

**Diagram Explanation:**

The diagram illustrates an allyl aryl ether structure, with the allyl group connected to an aryl (aromatic) group through an ether linkage. The aromatic ring has specific positions for double bonds, shown in the figure, which should be considered fixed when predicting the product of the Claisen rearrangement.

This exercise requires applying your knowledge of rearrangement reactions to transform the given structure accurately, keeping in mind electron movement and ring transition states.

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