ochem question again

[Pinbear]

---

Members don't see this ad.

The reaction of 1 mole of diethyl ether with hydrobromic acid results in the production of what?

I get one mole of ethyl alchol and one mole of ethyl bromide

but the Answer is 2 mole of ethyl bromide.

It seems like i need to add 2 mole of hydrobromic acid to get the answer.

I do not understand why the answer is 2 mole of ethyl bromide.

Can someone explain me this?

 

[oae]

KAPLAN BLUE BOOK Chapter on ETHERS:

Straight-Chain ethers can be cleaved are cleaved under ACIDIC conditions, usually under vigorous high temperatures

There fore 2 moles of HBr will add. So after you get your ethyl bromide and ethanol. The a second HBr will turn the ethanol into an ethyl bromide as well.

I know Br- substituting primary alcohol doesnt make sense, but in this situation it does.

 

[loveoforganic]

It makes sense if you realiZe the ethanol actually pretty much exists as ethanolium cation. I'd expect a fair bit of ethylene too though