Draw a mechanism for the acidic hydrolysis of the magnesium sa...

Question

Draw a mechanism for the acidic hydrolysis of the magnesium salt shown below to acetophenone.

Accepted Answer

Hello, everyone in this video and propose a possible mechanism for the hydraulic sis of the following magnesium salt to acetone under acidic conditions. So to produce ketones and how to hide from night trials, we first treated night trial with a free agent which results in information of magnesium salt of the means. So acidic, hydraulic sis of the salt produces the correspond how to hide or ketone. Let's go ahead and get started with our mechanism. So of course, we have this starting region right over here again because we're in acidic conditions, we have our molecule of H 30 plus. So we're going to go ahead and draw this out. So we have an auction with three hydrogen around it. And of course, we have, have a long pair and a former one plus charge. So what will happen is that the lone pair on the nitrogen will go ahead and pollinate itself and the bond between the oxygen and hydrogen will go ahead and break and form a lone pair, creating our molecule of H 20 which will go ahead and come into play later um part of our mechanism. So then our left side of this molecule, go ahead and remain untouched. So again, we have our H three C and then our carbon and H three C. Again, we'll have a double bound with nitrogen and we still have the M G I here. And then now this nitrogen will go ahead and contain one hydrogen. So we'll be pro tonight, of course, and the nitrogen will then have a plus one formal charge. So what we'll have in this case now is that our bond between our nitrogen and magnesium will go ahead and break and form lone pairs on this nitrogen. So basically what we're saying is that the M G I will go ahead and be a leaving group and the MG magnesium will have a plus one formal charge. So now will happen inside again, the left side of the molecule will go ahead and remain untouched. So two methyl groups here to abound still with our nitrogen having a long pair on the nitrogen and still having its proton. So then now will happen again, going back with the H30 plus, we'll go ahead and draw that in with a positive one formal charge. What will happen now is that again, the lone pairs on our nitrogen will go ahead and promenade itself. So it will be like so and the bottom of break forming a lone pair. So the product now is that we'll have again, left side remains untouched. So I'll go ahead and just redraw that and then we still have our double bound nitrogen. Now go ahead and have two protons again with a plus one formal charge. So now we'll go ahead and have sort of resonance structures. So what will happen is that the pi bond between the carbon and nitrogen will go ahead and break, forming a long pair on the nitrogen. And we'll go ahead and add the resonance arrow, of course, again, the left side remains untouched. So just leave it as is Alright. So now between the carbon and nitrogen is only a single bond, I still have the two protons and our long pair. Now the carbon on the left side, we'll go ahead and have a plus one formal charge. Remember the show that we produce now is going to go ahead and come into play. So the oxygen or the lone pairs on the oxygen of H20 will go ahead and come in as an electro file and attack this carbon right over here. So what will happen or produce is going to be as follows? So we'll have our right side now being remaining untouched. So we have the nitrogen with two protons and our lone pair and now carbon still has its two methyl groups. So I'll go ahead and add those in and now I will go ahead and have our water touch with as well. So, oh or H20 and the oxygen on our water will still have one long pair giving a plus one formal charge. Again, coming in with our H +20, the lone pairs from HBO will go ahead again, permit itself. So the bond between the oxygen and hydrogen is going to go ahead and break, forming lone pairs on this oxygen. So what will yield is going to be again? Left side is, or the right side is in touch, but we're gonna go ahead and flip it over. So are nitrogen on the left. Now with two protons still, of course, our lone pairs and we have the carbon with two methyl groups and now an O H group as well. So coming in with our H 30 plus, we'll go ahead and draw that in in a plus one formal charge will happen is that the nitrogen will go ahead and again, propagate itself. So we'll have the lone pair grabbing a proton and then the bond breaking to form a lone pair on the oxygen. So now what we'll have is again, our H R N R H, the bright side is and change C CH three ch three alcoholic group. Alright. So now on the nitrogen level have because we'll have one extra proton and then now this nitrogen will go ahead and have a plus one charge. And now what we can do is that The bonds from the war between the nitrogen and carbon will go ahead and break and form a lone pair on this nitrogen here. So what we see happening now is that we have our NH three group leaving and then will form this products as we have carbon, we have our ch three star metal, another CH three and then we'll have an oxygen and hydrogen. So a alcohol group, of course, we have two lone pairs on our oxygen. But the central carbon essentially here is going to be have a plus one formal charge. So what will happen is that the lone pairs on the oxygen will go ahead and reform a carbon neal group. So I double bound. So we'll have again, sort of like resonance structures. The residents arrows here, what we can see is going to be a CH three ch three double bound oxygen with the hydrogen still attached to it. So we'll have a oxygen having a plus one formal charge. Now, what will happen is that remember the NH three group that left, that's actually kind of scroll down here. So we have again, the N H three group that wasn't living group, essentially the lone pairs on that we'll go ahead and promenade itself. So then the bond between the oxygen and hydrogen will go ahead and break and form long pairs on this oxygen. So then the final product that we get is going to be where we have the H three C central carbon here. Another method grip on here and then double bound oxygen. So this right here is all going to be our plausible mechanism for this reaction.

Draw a mechanism for the acidic hydrolysis of the magnesium salt shown below to acetophenone.

Key Concepts

Acidic Hydrolysis

Mechanism of Nucleophilic Attack

Role of Magnesium Salt

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