Show how you would synthesize octanal from each compound.
You ma...

Question

Show how you would synthesize octanal from each compound. 
You may use any necessary reagents. 
(d) 1-bromoheptane

Accepted Answer

Hey everyone and welcome back into this video we are going to show how one bromo pension can be converted to hex Anel and provide any necessary regions. The starting material is one bromo pension so we are going to draw five carbon atoms 12345 and then at position number one we're going to add our bromo substitution. So that's the starting material and now we want to convert it to Jackson L. Hex Anel with essential corresponds to six carbon atoms and then at position number one we are going to add our Aldo hide right? So that's our first carbon atom which corresponds to an AL to hide group. Okay, we want to perform that conversion and we have to analyze this conversion a bit. The starting material is an L. Kill hey lied the final product is an AL to hide. There is no straightforward way to perform that conversion in a single step. So we have to be extra careful and first of all let's count the number of carbon atoms. The starting material has five. The final project has six. So that means we can take note that there must be an additional carbon atom carbon atom added to our chain. Okay so let's keep that in mind. Number two we want to make sure that we are forming an AL hide right, that's really important. The final functional group is an AL to hide and I'll kill. Hey light is really good for us is starting with cereal because it has a good leaving group. It has a promo substitution and one of the ways to add only one carbon atom is actually using cyanide to form a night trial. Now let's think if night trial would work for us, it looks like we have exactly the same chain. We're just adding one carbon atom. Right? And then essentially we're producing an album hide afterwards. So our logic might be the following one for me night trial first. And if we form a nitrile, is there any way that we can actually immediately convert it in channel hide? Actually yeah, there is. If we use our night trial and treated with dice a beetle aluminum hydride, then we will be able to get our al the hide. Of course we need to make sure that we are including our next reaction which is acidic hydro Eliza stuff. But let's not worry about it. We're just outlining our plan. So this is our whole goal. We understand that there will be only two steps involved. So let's see how that happens. First of all, we are going to convert our alcohol. Hey, light into night trial and to do that. We simply want to perform the following reaction because nitrile has CNN it. We want to use an appropriate nuclear file for an essence to reaction. Notice that this is a primary substrate, right? Because it's a primary substrate. We can use sodium cyanide which is a source of cyanide. Now, cyanide with a negative charge on carbon would act as a nuclear file. It would attack the electra Philip position followed by the loss of the leaving group. Right? And it would give us our night trial with that additional carbon atoms. So we are done with the first step we have our additional carbon atoms. So we can draw 12345 and then we are going to add that 61. We are going to say see and right, we have six carbon atoms. And this is a night trial. This is its corresponding AL to hide. So if you want to go from nitrile into an al tied immediately, we can see this as discussed before. We can use two steps step number one is addition of thy eyes of beetle aluminum high tribe. We want to make sure that our temperature is kept at negative 70 degrees Celsius. This is what you will see in the literature often. And the second reaction will be acidic workups. We're going to use H 30 plus to make sure that we are essentially converting our night trial into an alga hide. We're essentially reducing it. Right, remember that Diable age can be often used whenever you want to reduce an ester into an AL to hide or an acid chloride into an AL to hide as well as night trial into an AL to hide. No further reduction takes place. We essentially stop at an AL to hide. That's why Diable age is a very powerful choice here. So we clearly see our two steps. We can outline our synthesis. Let's label our synthesis and based on what we see here. The first step is to treat our L kill highlight with sodium cyanide, followed by the second reaction. When we take our nitrile formed and treat it with, that is a beautiful aluminum hydride, followed by acidic work up. This gives us a corresponding AL to hide. And based on this explanation, we can just say that the final answer to this multiple choice question is C. However, if you have any questions, feel free to drop your comment down below. Thank you for watching.

Show how you would synthesize octanal from each compound. You may use any necessary reagents. (d) 1-bromoheptane

Key Concepts

Nucleophilic Substitution

Carbon Chain Lengthening

Aldehyde Formation

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