Now we're going to discuss reactions of thiols. If you guys remember, thiols are the sulfur analog of alcohols, meaning that they look exactly like alcohols except that the oxygen is replaced with a sulfur. How is that going to change the molecule? Is it going to react just like an alcohol? Let's find out. So thiols are more acidic than a typical alcohol. If you think about it, that has to do with the fact that sulfur is a little bit bigger in size, and the size effect says that as the molecules get bigger, it's easier to give up an H and get a lone pair. So, thiols are going to contain a very acidic hydrogen. Okay. So what that means is that it's going to be easy to pull off that hydrogen and easy to make it a nucleophile after it's exposed to the base. So after you expose it to a base, pull off that hydrogen. It's going to be a great nucleophile. Just so you guys know, that nucleophile, once the sulfur has a negative charge on it, is called a thiolate. So a thiolate nucleophile is going to be capable of forming a few different reactions. That's what we want to go over right now. We can do sulfide synthesis through a thiol, and we can also do disulfide synthesis. Let's start off with the easier one, which is sulfide synthesis.
In sulfide synthesis, I start off with my thiol. That looks just like an alcohol except it's got the 'S'. And I react it with a base. The base is going to deprotonate the H and make my thiolate anion. Then that thiolate anion performs an SN2 reaction on an alkyl halide and alkylates. So, we wind up getting the sulfide, basically the analog to an ether, just with an 'S' instead of an 'O' for the ether. Let's go ahead and look at how this full mechanism, let's draw it out and make sure that we're all on the same page. So in my first step, my base is going to grab the acidic hydrogen of my thiol. Obviously, the hydrogen doesn't want 2 bonds, so I make a bond, I break a bond and I wind