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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

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

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.28P
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### 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.
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