[NewtoAtoms]

Hello Organic Chemists,

For the reaction carried out in basic solution, which one of the following species dissociaties to ethyl acetate?

[aldoxime_amine]

Those compounds are very difficult to isolate. Such a strange question to ask indeed...

I really don't want to give an answer to this question, but I would mechanically say option 2, others don't "look" anywhere "near" to ethyl acetate.

Note also that your ester would hydrolyze to the carboxylate.

[NewtoAtoms]

Actually I have worked them all in a basic solution and I am leaning towards d. Here's why:

       OH                                                   O-                                             O
       l                                                      l                                                ll
CH3-C-O-CH2CH3  + OH- ----------> CH3-C-O-CH2CH3 + OH- ---------> CH3-C-O-CH2CH3
       l                                                      l                                      THE DESIRED PRODUCT                                               
       H                                                     H

Is this mechanism entirely possible? 

Thank you for your help.

Newtoatoms

[sjb]

Actually I have worked them all in a basic solution and I am leaning towards d. Here's why:

       OH                                                   O-                                             O
       l                                                      l                                                ll
CH3-C-O-CH2CH3  + OH- ----------> CH3-C-O-CH2CH3 + OH- ---------> CH3-C-O-CH2CH3
       l                                                      l                                      THE DESIRED PRODUCT                                               
       H                                                     H

Is this mechanism entirely possible? 

Thank you for your help.

Newtoatoms

Not really, hydride is not a particularly good leaving group - do you see hydride loss when a nucleophile attacks an aldehyde? That's why 2 is a fair bit better, chloride is a much better leaving group.