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...
icon
Related questions
icon
Concept explainers
Question

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.

 

**Transcription for Educational Website**

**Title: 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. This reaction proceeds through a six-membered, cyclic transition state.

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

**Instructions**:
- 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 image depicts the chemical structure of an allyl aryl ether. This structure includes an aromatic ring connected to an ether group, which is further linked to an allyl group (shown as a linear chain with a double bond).

(Note: To explore the structural transformations and implications further, aspiring chemists can depict the bond shifts and the new configurations resulting from the Claisen rearrangement.)
Transcribed Image Text:**Transcription for Educational Website** **Title: 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. This reaction proceeds through a six-membered, cyclic transition state. **Task**: Draw the structure of the expected product when this compound undergoes a Claisen rearrangement. **Instructions**: - 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 image depicts the chemical structure of an allyl aryl ether. This structure includes an aromatic ring connected to an ether group, which is further linked to an allyl group (shown as a linear chain with a double bond). (Note: To explore the structural transformations and implications further, aspiring chemists can depict the bond shifts and the new configurations resulting from the Claisen rearrangement.)
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Ethers
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY