[Arees]

I need to make the following Ether using an Alcohol and an Alkyl bromide, could anyone help me out?

[voidSetup]

Check out the Williamson ether synthesis.  There are two possible answers but one would give better yields.

[Arees]

Yeah, I have, I unfortunately gave the response with the lower yield, and got 0.2/1 on the question, I'm really stuck finding what the other response is, could you help me out? I've still got one try on the question to get it right

[Honclbrif]

What was your alcohol, and what was your alkyl halide for your first response? How did you arrive at those structures? Is there any other way you could divide this molecule up to get a different alcohol and halide?

[quadsofdgods]

In my limited knowledge i have come up with the following possible reactants, i`m not sure if they are correctly named, i couldnt check the name of the structures i drew (which i`m sure where correct)

reaction 1
Sodium 1-methylcyclohexaoxide + bromocyclopentane

reaction 2
sodium cyclopentoxide + 1-bromo-1-methyl-cyclohexane

not a clue which gives a higher yield

[Arees]

The solution I gave was the following:



I got this message: Although some of the target ether might be obtained if these reagents were combined under acidic conditions, the 2° alkyl bromide could rearrange, and the 3° alcohol could decide to act as an electrophile as well as a nucleophile. There is a much better answer.

I'm looking at your responses guys, thanks.

[Honclbrif]

Did the question specify that this reaction was happening under acidic conditions, or did you chose acidic conditions as an option?

[voidSetup]

Yea Williamson ether synthesis can't be done under acidic conditions. My best guess would be to have a tertiary alkyl halide which dissociates, but that's a slow process and I'm not so sure it would be more efficient. Plus the alcohol would probably get protonated making it a worse nucleophile. Usually acid catalyzed ether synthesis uses 2 alcohols.

[Arees]

Honclbrif, I chose acidic conditions.

All it specifies is that one compound must be an alcohol, and the other an alkyl bromide

[Honclbrif]

Draw the mechanism of ether formation from an alcohol and an alkyl halide? What is acting as a nucleophile, what is acting as an electrophile? Would acidic conditions favor this, or disfavor this?