2. Complete the following OUTLINED reactions by supplying the missing reactants, reagents or products, as needed. Dees-Martin periodinane peracid migration: 1° > Me "H*" H2O MgBr 1) 2) H3O* hint: enamine

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
Question
### Organic Chemistry Reaction Task

**Task Description:**
Complete the following OUTLINED reactions by supplying the missing reactants, reagents, or products, as needed.

#### Reaction Details:

- **Reaction Part 1:**
  1. The starting material reacts with Dees-Martin periodinane.
  - The product of this reaction is an aldehyde group.
  
- **Reaction Part 2:**
  1. The aldehyde reacts with ethylmagnesium bromide (EtMgBr).
  2. The reaction intermediate is then treated with hydronium ion (H₃O⁺).

- **Reaction Part 3:**
  1. The product of the second reaction undergoes oxidation with a peracid.
  2. The reaction involves a migration step where primary groups (1°) migrate more favorably compared to methyl groups (Me).

- **Reaction Part 4:**
  1. The keto group possibly reacts in the presence of amine to form an enamine.
  2. The enamine formation is hinted at, involving acidic catalysis (H⁺) and water elimination (H₂O).

**Hints & Compounds:**
- The final product involves enamine formation.

**Graph/Diagram Explanation:**

- **First Box (Left, Top to Bottom):** This box represents the initial compound, which upon treatment with Dees-Martin periodinane is converted to an aldehyde.
  
- **Second Box (Left, Bottom):** The second box indicates the product formed after the Grignard reaction with ethylmagnesium bromide followed by acid workup that converts the aldehyde to a secondary alcohol.
  
- **Third Box (Middle):** The middle box shows the secondary alcohol that, upon oxidation with a peracid, forms a ketone through a migration reaction.
  
- **Fourth Box (Right):** The fourth box specifies the reaction forming an enamine, hinting at the use of an amine and involving an elimination of water.
 
By understanding these steps and the provided hints, we can fill in the missing details and complete the reaction pathway logically.
Transcribed Image Text:### Organic Chemistry Reaction Task **Task Description:** Complete the following OUTLINED reactions by supplying the missing reactants, reagents, or products, as needed. #### Reaction Details: - **Reaction Part 1:** 1. The starting material reacts with Dees-Martin periodinane. - The product of this reaction is an aldehyde group. - **Reaction Part 2:** 1. The aldehyde reacts with ethylmagnesium bromide (EtMgBr). 2. The reaction intermediate is then treated with hydronium ion (H₃O⁺). - **Reaction Part 3:** 1. The product of the second reaction undergoes oxidation with a peracid. 2. The reaction involves a migration step where primary groups (1°) migrate more favorably compared to methyl groups (Me). - **Reaction Part 4:** 1. The keto group possibly reacts in the presence of amine to form an enamine. 2. The enamine formation is hinted at, involving acidic catalysis (H⁺) and water elimination (H₂O). **Hints & Compounds:** - The final product involves enamine formation. **Graph/Diagram Explanation:** - **First Box (Left, Top to Bottom):** This box represents the initial compound, which upon treatment with Dees-Martin periodinane is converted to an aldehyde. - **Second Box (Left, Bottom):** The second box indicates the product formed after the Grignard reaction with ethylmagnesium bromide followed by acid workup that converts the aldehyde to a secondary alcohol. - **Third Box (Middle):** The middle box shows the secondary alcohol that, upon oxidation with a peracid, forms a ketone through a migration reaction. - **Fourth Box (Right):** The fourth box specifies the reaction forming an enamine, hinting at the use of an amine and involving an elimination of water. By understanding these steps and the provided hints, we can fill in the missing details and complete the reaction pathway logically.
Expert Solution
steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
Thioethers
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
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