The next reaction I want to look at is the addition of a secondary amine with carbonyl containing compound like an albohydrate ketone. In this case I'm using acetone and no, this is not a mistake. I left it there on purpose because as you might expect, this reaction is much like the addition of a primary amine. There's one large striking difference at the end. So I'm not going to go through all the mechanisms we just did because we're going to get protonate the carbonyl oxygen, attack by the nucleophile and we end up with an amino alcohol just like we did the last time and we're going to go from there. So now we still have our acid around and we're going to do the same thing we did last time. We're going to protonate the oxygen of this amino alcohol. When we do that, we again get the same species we had last time. We have an amino group attached to a carbon along with a hydroxyl that's now been protonated to give a very good leading group and that is water. We can do the same thing we did last time. We're going to push these electrons into the form of carbon nitrogen double bond and the carbon oxygen bond is going to break hydrolytically with the electrons going with the oxygen and that gives us the same compound we had before which is an amineum compound. There's one difference though. One slight difference. Remember last time we got to the amine by pulling a proton off of the nitrogen only now there are no protons in the nitrogen. So what is going to happen here? Is this reaction just going to go back and no reaction occurs? No. Never forget that it grows bins rule. It's just put all of the relative hydrogens on. So this is a methyl group on this side. This is also a methyl group and that's where we're going to get our hydrogens from. Notice this is also a CH3 group but I've put one of the hydrogens out because I'm going to pull that proton off with my base. In this case I'm going to use water as my base where you're going to pull that proton off. Oops. That was a bad mistake. Actually we could have proceeded but we don't need to. The electrons in the carbon hydrogen bond are going to form a carbon carbon double bond and when we do that we have to get rid of the carbon nitrogen double bond. They're going to come up onto the nitrogen and we form this species. And we call this thing an enamine. So the reaction proceeds normally. In fact it proceeds the same way as a primary amine would right up to here and at this point we don't have a proton that we can pull off of the nitrogen. So we have to pull it off to someone else. Notice now that for this reaction to proceed at least one of the alpha carbons that is either this carbon or this carbon must contain a hydrogen atom in order to proceed to the enamine.