[heisenbergscat]

Will the reaction between Sodium Ethoxide and 1-bromohexane yield an SN2 or E2 reaction? The product was then treated with toluene. Will the product result in the formation of 1-hexene, ethyl hexyl ether (1-ethoxyhexane), or both? Much appreciated.

[Archer]

What are your thoughts? What is the mechanism for each potentially competing reaction?

[heisenbergscat]

I feel it would lean towards SN2 because most primary alkyl halides undergo nucleophilic substitution due to decreased steric hindrance with a good nucleophile such as sodium ethoxide. Correct me if Im wrong.

[Archer]

Ethoxide is a strong nucleophillic base, therefore it is possible for both to occur. What other factors in the experiment might influence the products? 

[heisenbergscat]

Here are the mechanisms.

[Archer]

A more simple question; in the absence of a catalyst what determines whether or not a reaction will initiate?

[heisenbergscat]

Well in this experiment, sodium ethoxide and hexyl bromide were heated to reflux at the boiling temperature of around 154'C (BP of hexyl bromide).

[Archer]

Well in this experiment, sodium ethoxide and hexyl bromide were heated to reflux at the boiling temperature of around 154'C (BP of hexyl bromide).

If that temp exceeds the activation energy for E2 reaction then you will have at least some competing reaction taking place.

[heisenbergscat]

So I understand that when more heat is applied, the E2 product gradually increases relative to SN2, if the activation energy of E2 is reached. So it is possible that both products have formed in the aforementioned experiment?

[Archer]

So I understand that when more heat is applied, the E2 product gradually increases relative to SN2, if the activation energy of E2 is reached. So it is possible that both products have formed in the aforementioned experiment?

E2 reactions of primary halides generally require strong base and heat if the strong base is also a nucleophile.

I don't know what happens experimentally, theoretically the elimination product should be present.