Synthesis of keytones/aldehydes from ethanol formed from E1 (alkoxide reagent)?

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    Ethanol Synthesis
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Discussion Overview

The discussion revolves around the feasibility of synthesizing aldehydes or ketones from ethanol produced via an E1 reaction involving a tertiary haloalkane and sodium ethoxide. Participants explore the practicality and efficiency of this synthetic route, considering alternative methods for obtaining ethanol and the implications of using various reagents.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant questions the feasibility of using a tertiary haloalkane with sodium ethoxide to produce ethanol, which could then be oxidized to aldehydes or ketones.
  • Another participant confirms that the proposed reactions are possible.
  • A different participant critiques the approach as potentially wasteful, highlighting the economic and practical drawbacks of using expensive reagents to produce cheaper ones, such as ethanol.
  • This participant suggests that purchasing anhydrous ethanol directly may be more efficient than synthesizing it through the proposed method.
  • Additionally, the same participant mentions that the products of ethanol oxidation, acetaldehyde and acetic acid, are also inexpensive and readily available.
  • Another participant offers an alternative method for producing ethanol through the fermentation of sugar with yeast.

Areas of Agreement / Disagreement

Participants express differing views on the practicality and efficiency of the proposed synthesis route. While some acknowledge the possibility of the reactions, others argue against the method's economic viability, indicating a lack of consensus on the best approach.

Contextual Notes

The discussion highlights assumptions regarding the cost-effectiveness and practicality of various synthetic routes, as well as the potential need for purification of ethanol and the implications of using different reagents.

Who May Find This Useful

Individuals interested in organic synthesis, particularly those exploring alternative methods for producing alcohols and carbonyl compounds, may find this discussion relevant.

cp-svalbard
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No, this isn't a homework question...

Would it be feasible to use a tertiary haloalkane with sodium ethoxide, then use the ethanol formed from the deprotonation of the haloalkane in the E1 reaction for the synthesis of aldehydes or keytones?

Just thinking it could be an alternative way, since the ethanol formed is usually not the target compound of an E1.

Now that I'm thinking about it, since ethanol is a primary alcohol it would probably be oxidized to a carboxylic acid if you used jones/PCC ??
 
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Yes. It is possible for the reactions you stated to occur.
 
You could do this, but you might earn a medal for the most wasteful synthesis of the year (no offense intended to you personally, it's a joke!)

Many reactions are possible, but only a select few are used because they are a) economical b) safe and c) practical. Sodium ethoxide is worth much more than ethanol, so you're converting an expensive reagent (actually, two if you're going to waste a tertiary alkyl halide too!) to a cheap reagent. On top of that, you will have to separate your E1 product from your ethanol and then purify your ethanol before you can use it in subsequent reactions. All of this is time, resources, money, and energy, when you could simply buy 95% ethanol and dry it with, for example, magnesium sulfate, to get anhydrous ethanol. Furthermore, the aldehyde and carboxylic acid formed from ethanol, acetaldehyde and acetic acid, respectively, are ALSO very cheap and common reagents. To prepare them yourself serves no real purpose.

If you want to make ethanol, though, maybe the best (and cheapest) way is by hydration of ethylene.

Of course, if you want to minimize waste from reactions, it might be worthwhile to try to recover your ethanol. However, your uses for it will be limited unless you purify it and analyze it. Again, the cost/benefit ratio may not be favorable.

It's nice to do these kinds of reality checks when you're thinking about syntheses :)
 
Last edited:
The easiest way to make ethanol is to ferment sugar with yeast.
 

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