For each compound, give the product(s) expected from (1) HgSO

Question

For each compound, give the product(s) expected from (1) HgSO₄/H₂SO₄ - catalyzed hydration and (2) hydroboration–oxidation.

a. hex-1-yne

Accepted Answer

Hey everyone and welcome back in today's video. We are going to solve the following problem for the compound shown below predict products that result when it undergoes the following a acid catalyzed hydration. Be hydro operation, oxidation, the starting material is and al kinds use the presence of that triple bond. And we understand that we have two reactions and acid catalyzed hydration. So let's start with this one. We may simply withdraw our alkaline. How many carbon atoms do we have? We have 1234. That's one beat sign, right? Because the triple bond starts at carbon number one, so we may simply draw our triple bond and two more carbon atoms. That's our starting material. We understand that this is a terminal alkaline because it doesn't have an al Kielce obsession over here responded directly to hydrogen. So this seminal al kind is treated in an acid catalyzed hydration reaction. Basically we can say that an acid catalyzed hydration requires us to use water in the presence of a strong asset which is generally sulfuric acid in an acid catalyzed hydration mechanism. Let's remember that an acid catalyzed hydration follows the electra. Feel like edition mechanism in which we have to follow the more cosmic of radio chemistry and that means we are taking one of our pi bonds and we're going to add hydrogen to a less substituted position because this position doesn't have an alcohol substitution, it's it's less substituted. So we're going to add hydrilla disposition and the alcohol group will be added to a more substituted position. So what we're forming is simply a double bond Now, because one of the pi bonds has been used, we may draw a four member chain with the double bond starting at position one. And we understand that position number two now has an alcohol group, but because this is an Enel that we have just formed, we have to recall that it's unstable and it undergoes total memorization to produce a more stable ketone. So the equilibrium shifts significantly towards the formation of a ketone. And essentially what we're going to do, we're going to transfer that acidic proton over here to turn this into a metal group and then we are going to form a carbonell group over here. There'll be a double bond carbon auction double bond. And if we draw that We have our four member chain and then the carbonell group at position number two. Right, This is our final product, We can say that we have successfully formed our first product. The product for a is our key tone. Now, thinking about reaction be the main difference is that we are using hydration oxidation. Same terminal alkaline with four carbon atoms. Hydro abrasion oxidation implies that we're using boring in the presence of tetra hydro Furin followed by the treatment of this al kind with hydrogen peroxide in hydroxide. And if you think about this reaction, recall that hydro operation oxidation implies the anti more cosmic of regional chemistry A. M. R. So that's the whole difference. Instead of adding hydrogen to a less substituted position. We're going to add it to a more substituted position and the alcohol group will go to a less substituted position. So we are reversing these two. In other words, we are switching our rule to the ante Markovic of rule and that's why we're adding alcohol to position number one instead of position number two. And when we think about it we can just draw our four member chain and carbon number one now will have an alcohol group. So we're going to add an O age group and there is still that double bond between carbons one and two. Right? Because the remaining pi bond is unaffected, meaning there is a double bond at this position. And once again this is an Enel because it has a double bond and the adjacent alcohol group, meaning it's not so stable. And in this case we will have an equilibrium between an email form and an alga hide. And since al hides were heat zones, their carbon compounds, they're more stable. We will have that totem tourism in which that hydrogen atom will be transferred over here to get rid of the double bond and we will form a carbon steel compound over here. So let's see how that looks like. Essentially we're going to draw our al to hide groups. There will be a carbon oxygen double bond er is that implicit hydrogen atom over here. Right? So we're going to add it as well. There'll be hydrogen. This is our carbon number one and then we have 123 more carbon atoms. So let's add them 123. So this will be our final adult height. Right, let's count how many carbon atoms do we have? 1234, 1234. Well done. So we got to have a final product. Let's label it as our final product for B. And we may now discuss our findings. So we looked at a terminal AL kind and we looked at two different reactions and acid catalyzed hydration and a hydro abrasion oxidation reaction. We understand that for a It follows a more cosmic of retail chemistry for be it flows the ante Markovic of radio chemistry in particular. It doesn't really matter which rule we use whenever we are dealing with internal AL kinds, but because this al Qaeda is terminal, it does matter because the substitution is not equivalent on each end of the triple bond. And this is clearly seen by the addition of the hydroxyl group at two different carbon atoms. Right? We have formed two different emails. The first email was formed with ohh, position two and the second email was formed at position number one giving us a more stable key tone for A and a more stable AL to hide for B. So these are our final products and we may simply conclude that the correct answer choice to this multiple choice question is A. However, if you have any questions, don't hesitate to leave your comment down below in the comment section and thank you for watching.

For each compound, give the product(s) expected from (1) HgSO₄/H₂SO₄ - catalyzed hydration and (2) hydroboration–oxidation.
a. hex-1-yne

Key Concepts

Catalytic Hydration of Alkynes

Hydroboration-Oxidation

Markovnikov's Rule

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