Strong reduction of organic acid group

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Discussion Overview

The discussion revolves around the reduction of carboxylic functional groups in organic synthesis, specifically exploring methods to completely reduce these groups to hydrocarbons. Participants consider the implications of such reductions for polymerization processes and the challenges associated with using certain catalysts or reagents.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant seeks a method to completely reduce a carboxylic acid to a hydrocarbon without using harsh chemicals or expensive catalysts.
  • Another participant suggests that converting the acid to an ester might be a simpler approach.
  • A third participant argues that it is generally easier to esterify or amidify an acid than to remove a carbon-carbon bond, referencing a previous answer from another user.
  • The original poster clarifies that they need to remove the oxygens entirely and expresses uncertainty about the possibility of full reduction.
  • Another participant prompts the original poster to specify their monomer and consider that other functional groups in the molecule may be sensitive to reduction.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the best approach to achieve the desired reduction, with multiple competing views on the feasibility and methods of reduction remaining unresolved.

Contextual Notes

The discussion highlights the limitations of the proposed methods, including the potential sensitivity of other functional groups in the polymerization process and the lack of clarity on the specific structural requirements for the desired outcome.

Who May Find This Useful

Researchers and practitioners in organic chemistry, particularly those focused on synthesis and polymerization processes, may find this discussion relevant.

chad kimsey
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I've been thumbing back through my organic synthesis book to try and remember how to reduce a carboxylic functional group. I know how to do partial reduction to primary alcohols, or create aldehydes and or acyl halides. But isn't there a way to completely reduce it all the way to a hydrocarbon without too much trouble and nasty chemicals or expensive PtO catalysts? Haven't found a way yet...just wondering if anyone out there knew how to do this I'm trying to prep an organic species for polymerization, but the acidic group is a reactive site and I do not want the other monomers to bond there so I need to get rid of it completely
 
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Wouldn't it be easier to convert it into an ester?
 
Yeah, its almost never easier to get rid of a c-c bond than it is to esterify or amidify an acid. There's a half-dozen other acid-base masking reactions you could also do. I think DrDru answered this. It should be closed.
 
I'm trying to remove the oxygens, an ester is not the product I need. I may have to try a different structural molecule for the polymer i have in mind...I was thinking it could fully be reduced but can't remember how.
 
Maybe you could specify your monomer and what you really want. If you want to do a polymerization, your molecule probably contains other groups sensitive to reduction.
 

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