Orgo Question Substution vs Ethers?

[DonExodus]

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Im having problems knowing when a regular substitution will happen, vs an ether formation.

Say I have:
ROH + R'X

Will it be:
ROH + R'X ---> R'-OH
or
ROH + R'X ----> R-X
or
ROH + R'X ---> R'-O-R ?

How can I tell if its going to form an ether, an alcohol, or an alkyl halide?
What will make it tend to form an ether?

Topscore-
CH3-CHBr-CH2-CH3 + CH3-OH -----> CH3-C-(CH2CH3)-O-CH3 as the correct answer, DESPITE the RX being secondary, which is a nono for the Williamson.

 

[allstardentist]

I think the solution from topscore is correct regarding the williamson ether synthesis.

 

[DonExodus]

I think the solution from topscore is correct regarding the williamson ether synthesis.

My chem book and all other resources say the RX MUST be primary.

 

[phoebaly]

The Williamson proceeds by the SN2 mechanism with and alkoxide being formed from the alcohol. That means that primaries will react best but secondary alkyl halides will also react giving the elimination product as well as the ether. It is still possible to form the ether. It will just need to be purified.