 Okay, so let's try another mechanism here or learn another mechanism So if we have a primary alcohol like butanol here And we react it with fine ill chloride. That's this SOCl2 business, okay fine ill chloride you're going to Substitute the OH group for a CO, okay? so this reaction When you react it with a primary alcohol is going to do that SN2 reaction as the last step again So let's go over the mechanism this ether here. That's just the solvent. We don't have to worry about Everybody got this written down. Can I So fine ill chloride I don't think you've seen already, but you should be able to Try to draw the structure and have a pretty reasonably good guess at it I'm going to draw it like this even though If I post this on YouTube, which I will people will be like, huh, there's not really a double bond in between that sulfur But it's easier for you to think about it. I'll still post this don't I ain't afraid of the haters Okay, and I'm going to explicitly show those electrons on my oxygen there So just to go back to what I was saying Usually when you have the sulfur oxygen double bonds the better Resonance form is that But it's easier to see the mechanism doing it this way and it's hard hard for Introductory organic students to deal with that permanent Okay, so the first step is that the nucleophile here is going to react with the electrophile The nucleophile being the alcohol the electrophile being the thionyl chloride Specifically going to react At the sulfur of the thionyl chloride. Okay, so what we're going to do is take those oxygen electrons attack the sulfur and make that double bond Electrons go up to the oxygen kind of like what it looks like in that other resonance Okay, so I want you to try to draw that on your own While I'm drawing it up here and tell me Did you get it right? Is that what you drew? Or would have drawn did you get it? No, yes Now draw the product is that what you would have drawn Remember just do what your arrows are showing and you'll get it right every time The next thing is we got to get one of these chlorines Ah Okay, I'm going to erase this Because that one of these chlorines is going to come back and do that SN2 reaction at the end So what we're going to do is take these electrons Make that double bond again, and that's going to kick off the Chlorine as a leading group So I put the chlorine up there up at the top because it's going to I want to show that back Questions on anything so far Does it make sense? Okay, so now here's the SN2 part Okay, so the chlorine is going to come And attack from the back side of this big leaving group everybody okay with that and Then we're going to actually make a Couple of other little pieces here the leaving group just doesn't leave like that We're going to make that double bond there in between the sulfur and oxygen and Doing that is going to kick off the last chlorine now the important part of our reaction is done We've made the alkyl chloride like what we were looking for I'm going to draw it like that just to emphasize that it came from the other side We've also made protonated sulfur dioxide Hopefully you wrote that And then the cl-minus as well you could think of this cl-minus as deprotonating that Hydrogen and that's like the last step Even though we already got the molecule we were looking when we do that. We get SO2 Hopefully I'm not off the video range Am I? Okay, yeah, I mean as long as the board is that yeah, that's all that matters Okay, here we could do this like I say this is the part we were really looking for questions on this mechanism Fine alkyl chloride reacting with the primary alcohol. Okay