I had to react 1-propanol with NaBr and H2SO4. I refluxed for one hour and when attempting to separate out the product (product was supposed to be 1-bromopropane) via sep funnel either could no longer distinguish between the organis layer and the aqueous layer, or there was never a layer to begin with.

Question

I washed it with water, and two 15ml washes of sodium bicarbonate.

I was alloted 8grams of starting material and that was all. I used about 2grams of the 1-propanal and tried this reaction four times, why did it not succeed?

Answer 1

I wasn't there to watch every step so I really can't say; however, this is a fairly standard reaction. I suspect it actually occurred and you failed, somehow, to capture it.

Answer 2

I added about 5g of NaBr, and used about 20ml of sulfuric acid. I did this reaction four times, making sure my 1-propanol was my limiting reagent. I'm not sure where I could have gone wrong. It is a possibility that during the reflux stage the temp got too high and I may have accidentally boiled off my product?

Answer 3

Any guess on my part are pure speculation so it's better if I don't speculate.

Answer 4

I would actually appreciate some speculation. I have to write an article over this reaction, and if it failed, then why. I have some theories such as I reacted everthing at too high of a temperature and lost product, poor leaving groups involved... yadda yadda.

I would like to better understand what exactly is happening with this reaction and why it is so difficult. All of the classes had people doing this reaction and only a small percentage has been able to succeed.

Answer 5

PLEASE assist