OH Swern or Dess-Martin

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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...
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  1. The Dess–Martin reaction reacts an alcohol with the Dess–Martin periodinane. The first step displaces one of the acetate groups on the periodinane with the alcohol. A base then deprotonates one of the alpha protons, forming a new carbonyl bond, iodinane and acetic acid. The oxidation stops at this stage to give the aldehyde.

Both Swern and Dess–Martin conditions will also convert a secondary alcohol to a ketone.

Now apply what has just been discussed.

Draw the major organic product.

The Dess-Martin reaction reacts an alcohol with the Dess-Martin periodinane. The first step displaces one of the acetate
groups on the periodinane with the alcohol. A base then deprotonates one of the alpha protons, forming a new carbonyl
bond, iodinane and acetic acid. The oxidation stops at this stage to give the aldehyde.
Both Swern and Dess-Martin conditions will also convert a secondary alcohol to a ketone.
Now apply what has just been discussed.
OH
Swern or Dess-Martin
Draw the major organic product.
Select Draw Rings More
G
→
с H O
Erase
2 Q
Transcribed Image Text:The Dess-Martin reaction reacts an alcohol with the Dess-Martin periodinane. The first step displaces one of the acetate groups on the periodinane with the alcohol. A base then deprotonates one of the alpha protons, forming a new carbonyl bond, iodinane and acetic acid. The oxidation stops at this stage to give the aldehyde. Both Swern and Dess-Martin conditions will also convert a secondary alcohol to a ketone. Now apply what has just been discussed. OH Swern or Dess-Martin Draw the major organic product. Select Draw Rings More G → с H O Erase 2 Q
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