How to Convert Acetic Acid to Propanoic Acid Without Cyanide?

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Discussion Overview

The discussion revolves around methods to convert acetic acid to propanoic acid without using cyanide. Participants explore various chemical approaches and reactions involved in the transformation, focusing on chain homologation techniques.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant suggests avoiding cyanide in the conversion process.
  • Another asks for additional methods of chain homologation that could be applicable.
  • A participant proposes using acetyl chloride followed by N-methylethanamide to increase the carbon chain, but expresses uncertainty about how to remove nitrogen and introduce a hydroxyl group.
  • Another participant questions the proposed use of N-methylacetamide, indicating it may not have the correct carbon backbone for the intended transformation.
  • A later contribution suggests an alternative route involving acetyl chloride, diazoketone, and Wolff rearrangement, followed by the addition of water, but acknowledges being stuck on how to incorporate the necessary carbon.

Areas of Agreement / Disagreement

Participants present multiple competing views and methods for the conversion, and the discussion remains unresolved regarding the best approach.

Contextual Notes

Some assumptions about the feasibility of proposed reactions and the specific conditions required for each method are not fully explored or clarified.

deep838
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Without using a cyanide
 
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What other methods of chain homologation do you know?
 
i was thinking of acetyl chloride and then N-methylethanamide... that will give me 3 carbons... but then how to get rid of nitrogen and bring OH?
 
Can you draw some structures? Seems like N-methylacetamide has the wrong carbon backbone too.
 
yeah... that's where I'm stuck... i really have no idea on how to bring the carbon inside!

how about this:
acetyl chloride then diazoketone then wolff rearrangement and then water! right?
 
Last edited:

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