Question

Why doesn’t a reaction take place between trans-1,3-pentadiene and Na+EtOH- in EtOH?

Why doesn’t a reaction take place between trans-1,3-pentadiene and Na+EtOH- in EtOH?
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Answer #1

In Na+EtO-, the EtO- part acts as base. Actually in major reactions, ethoxide is used as a base to abstract acidic protons, where using convensional OH-  is difficult. So, it will react if there is an acidic proton.

In 1,3-pentadiene,

there is no acidic protons at all. You can argue that the shown H will have an enhanced acidity because bringing negative charge there will induce resonance in the species. But, the pKa of that proton is not so low, that it can be abstracted by a base of average strength like EtO-. So there eill be no acid base reaction.

There will be nucleophilic attack by EtO- also, since diene is an e- rich system and nucleophilic attack on e- rich system is ot feasible.

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