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

[cp-svalbard]

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 ??

 

[aspiring_one]

Yes. It is possible for the reactions you stated to occur.

 

[DDTea]

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 :)

 

[chemisttree]

The easiest way to make ethanol is to ferment sugar with yeast.