[svalbard]

Just kind of curious.

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 fro 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 ??


 

[rabolisk]

I'm not sure I understand how ethanol would form from the "deprotonation of the haloalkane in the E1 reaction" .

[rabolisk]

Nevermind, I guess I can see how this would occur. Nevertheless, E1 is usually not useful because it is in competition with SN1. In this case, I also think E2 would occur because ethoxides are strong bases. But really, if you had sodium ethoxide, you would just add water to it to get ethanol (equilibrium conc.), I would think.

[svalbard]

Yeah, scratch the E1 i miss typed. Obviously it would be an E2 since strong bases are not used in E1 and it is usually just a side reaction occurring.

Yeah there are easier ways to make ethanol, this would sorta be the going around your @#^ to get to your elbow way