Oxidizing Primary Alcohol to Aldehyde in Methylenechloride & DMF

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SUMMARY

The oxidation of primary alcohols using Pyridinium dichromate (PDC) in Methylene chloride results in the formation of aldehydes, while the same reaction in Dimethylformamide (DMF) leads to the production of carboxylic acids. The key factor influencing this difference is the hygroscopic nature of DMF, which often contains water, facilitating the formation of aldehyde hydrates that further oxidize to acids. This highlights the importance of solvent choice in oxidation reactions.

PREREQUISITES
  • Understanding of oxidation reactions in organic chemistry
  • Familiarity with Pyridinium dichromate (PDC) as an oxidizing agent
  • Knowledge of solvent properties, specifically Methylene chloride and DMF
  • Basic concepts of aldehyde and carboxylic acid formation
NEXT STEPS
  • Research the mechanism of oxidation reactions using PDC
  • Study the effects of solvent polarity on reaction outcomes
  • Explore the properties and applications of Dimethylformamide (DMF)
  • Investigate alternative oxidizing agents for primary alcohols
USEFUL FOR

Chemists, organic synthesis researchers, and students studying reaction mechanisms in organic chemistry will benefit from this discussion.

Mop
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My problem is to describe the reason why a primary alcohol with
PDC in Methylenechloride is oxidized to the aldehyde, but in DMF further to the Acid. Would the only reason be that DMF is hygroscopic and contents usally some water to give the aldehydehydrate?
 
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