Which Will Undergo Faster Williamson Ether Synthesis?

[Suraj M]

Homework Statement

Which will undergo faster Williamson ether syntehsis
It was either faster or better, I'm not sure

A)3-Chlorobutan-1-ene
B)1-Bromobutane

Homework Equations

The Attempt at a Solution

I thought option A because of its alylic position it will form a stable carbocation (and through SN1)
Is it correct? Or is it B because bromine is more weakly bound to the primary carbon

Thank you :-)

 

[Ygggdrasil]

What mechanism is involved in Williamson ether synthesis, SN1 or SN2? What factors are most important for reactions of that type?

 

[Suraj M]

The mechanism depends on the reactants right?
What factors? I'd say driving force of the stabilized carbocation if it's SN1 else steric factor and strength of the CX bond for SN2?
Is that right?

 

[Ygggdrasil]

The mechanism depends on the reactants right?

You should double check what your text says about the mechanism of Williamson ether synthesis.

 

[Suraj M]

Oh always SN2?
Then in that case it's option B right?

 

[Ygggdrasil]

Yes. If you were to try to form an ether via an SN1 reaction, you would probably have too much competition from the E1 product.

 

[Suraj M]

Ah okay
Thanks Ygggrasil ! :-)