Show how you might synthesize the following compounds, using a...

Question

Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your starting materials. If the compound given cannot be synthesized by this method, explain why.
a. hex-1-yne
b. hex-2-yne
c. hex-3-yne

a. hex-1-yne

b. hex-2-yne

c. hex-3-yne

Accepted Answer

hi everyone show which hey lights can be used with a settling as a starting material to synthesize the following compounds for a we have pant one iron. Now, first of all we are starting with a settling. So for a we control the structure of a settle in. It's the simplest alkaline. So we have two carbon atoms bonded by a triple bond. And because we are forming a longer chain al kind, we simply wish to d protein it at first and then form a good nuclear file out of it. Recall that there are acidic hydrogen on each end of the triple bond. So in particular here we may expand one of the acidic hydrogen and first of all we are D protein eating it using a strong base And we are commonly using sodium amid. This is a very common region for the deep protein nation of these acidic hydrogen in all kinds. So the base the protein. It's that. And we are forming our new club file. We made through it now with a negative charge because this is a nuclear file with a negative charge is a strong nuclear file. And therefore we are dealing with an essence to reaction on words If we wish to synthesize Plant 1, 9. So that means we have a triple bond With three more carbon atoms. Because Pan one I means five carbon atoms in the parent chain. We may notice that the additional number of carbon atoms that we are adding is three. That said we wish to have a substrate with three carbon atoms and a good leaving group because that's in essence to reaction. And therefore the substrate that we may use would have three carbon atoms and a good leaving group bonnet said the good leaving group that we could choose here would be brahman in such a reaction. The negative charge with attack the electra Felix center. And simultaneously we would have the loss of the leaving group to indeed produce our product and one line. So the substrate that we are proposing here is one bromo propane. Good job. We have our first answer. Now if we look at B we wish to synthesize beat to iron. We already know that our first step is to produce the nuclear file and we are using a settling with sodium. I mean to produce the new cloud file again, we will be dealing with An sn two reaction and we wish to produce beat to iron. So we have a triple bond with two carbon atoms. We need two more because we have been detained as our parent chain but in this case that would mean we would add one carbon above and one carbon below. Since we have a total of four carbon atoms and the position of the triple bond is starts at position C. Now that tells us that we first will wish to add a muscle group on top and another metal group on the bottom meaning we will have to D. Protein nation steps so we have to perform it step by step. First of all, we may use that nuclear file form and we need a primary substrate for an essence to reaction ideally because we need to add just one metal group. We may use muscle bonded to a good leaving group. Let's suppose prom in again. So we may use H. Three CBR. The nuclear file will attack the electra Felix center for by the loss of the leaving group. And we will form our first product. This is our intermediate product in which we are now attaching a muscle group. However, we need to make sure that this is butte to iron. And therefore we are repeating the D. Protein nation. Stop we are again adding sodium amid two d. protein ate the alkaline and we are producing another nuclear file with a negative charge. And similarly, since we need another method group bondage it, we will just add another molecule of methyl bromide. This is an essence to reaction in which the negative charge again attacks the electra Felix center. And we have the loss of the leaving group. And indeed we are producing our final product. After this step we get B. T. Time. So that's that for B. We actually needed to moles of muscle bromide. That's our al kill. Hey light for this part. Great job. And for the final one we wish to produce pent to iron. Now again, if we start with a settling, we made troy settling as our starting material. We are deep rotating it using sodium amine. And if we think about the structure that we get here, nothing is real different. That's our nuclear file. We need an essence to reaction in which we produce tends to iron. So if we draw pen to iron first of all, the triple bond would connect positions two and three, meaning there will be a method group. We have a total of three carbon atoms. We need two more so we will have one too. And if we compare these structures we need to add one substitution being a methyl group and another substitution being an ethyl group. So to do that again, we will need to perform the reaction twice. In the first step, we may just use the previously used methyl bromide. The nuclear file will attack the electra Felix center. We will have the loss of the leaving group forming the intermediate product. So that would be triple bond bon appetit method group. And now we are d protein eating it. Once again, we're using another equivalent of sodium a mead to remove that additional acidic hygiene. And we are forming our nuclear file for a lesson to reaction. Now this is where we need to add an ethyl group. So to add an ethyl group, we need to use two carbon chain bond. It's a good leaving group. So again, we can choose booming and notice that the negative charge would essentially attack the electra filic center and we would have the loss of the leaving group in this stab. We would produce pan to iron. Notice that after this reaction we need return to pen to iron. We have added a method groups and an ethyl group. So we may conclude that we need two regions, 1 mole of muscle Bromide and one more half bromo ethane. So these would be our final regions. For C. Now summarizing our findings, we may say that for a we needed one bromo propane for B. We needed to most of metal bromide and for C we needed one mole of methyl bromide and one mole of bromo bromo essay. The correct answer for this multiple choice question is A And if you have any questions, don't hesitate to leave them down below. Thank you for watching this video.

Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your starting materials. If the compound given cannot be synthesized by this method, explain why.
a. hex-1-yne
b. hex-2-yne
c. hex-3-yne

Key Concepts

Alkyne Synthesis

Markovnikov's Rule

Rearrangement and Isomerization

Watch next

Show how you might synthesize the following compounds, using acetylene and any ­suitable alkyl halides as your starting materials. If the compound given cannot be ­synthesized by this method, explain why. a. hex-1-yneb. hex-2-ynec. hex-3-yne

Key Concepts

Alkyne Synthesis

Markovnikov's Rule

Rearrangement and Isomerization

Watch next

Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your starting materials. If the compound given cannot be synthesized by this method, explain why.
a. hex-1-yne
b. hex-2-yne
c. hex-3-yne