I'm pretty sure that they can be distinguished, as a benzlic carbocation is the most stable, while phenol will not create a carbocation (I think it would be an aryl, or something along those lines). Be careful in taking what you read in prep books as fact, there are many errors in them!laya533 said:Why cant we distinguish between a benzyl alcohol and a phenol by disolving them in HCl? I thought its the lucas test and we can do it to distingyish them.
This is true, but I assume that the question said Lucas Reagent and not just HCL? If not, the previous poster is correct, you need a catalyst.liverotcod said:The Lucas test requires a zinc chloride reagent, in addition to the HCl.
An easy way to think about it is the ability of the two leaving groups involved. Which is a better leaving group: -Cl or -OH? Cl is a much better leaving group and will not displace -OH.laya533 said:No, it did not ask about the lucas. It just said that these 2 compounds cannot be seperated based on their activity with HCl. But I think we can. Why am I wrong?
To my knowledge you could see which compound is more acidic. Phenol should be more acidic than benzyl alcohol.laya533 said:Why cant we distinguish between a benzyl alcohol and a phenol by disolving them in HCl? I thought its the lucas test and we can do it to distingyish them.
1. What is the context of this statement?laya533 said:It just said that these 2 compounds cannot be seperated based on their activity with HCl.
2. Technically, the benzyl cation is a primary carbocation, but its stability is close to that of t-butyl carbocation b/c of resonance stabilization. So you can't go strictly by the primary < secondary < tertiary hierarchy of stability for aromatic carbocations. Which leads to my next point...adiddas125 said:In benzyl alcohol it looks like it will be a primary carbocation when H2O leaves, and will become a secondary carbocation if, water leaves from this compd.