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Study the reaction scheme for the synthesis of compounds 2 and 3 fron compound shown below and answer the following questions:AczoOAcOHAczo Iz04:1 ratioHand draw me...

Question

Study the reaction scheme for the synthesis of compounds 2 and 3 fron compound shown below and answer the following questions:AczoOAcOHAczo Iz04:1 ratioHand draw mechanism for the conversion of 'pyridine to Compound B

Study the reaction scheme for the synthesis of compounds 2 and 3 fron compound shown below and answer the following questions: Aczo OAc OH Aczo Iz0 4:1 ratio Hand draw mechanism for the conversion of 'pyridine to Compound B



Answers

The following questions are based on the reactions of acetophenone (19) shown here. (Sections 23.3 and 23.4) (a) Draw the structures of organic compounds 20 and 21 (b) Give a mechanism that explains how 19 is converted into 22 (c) Suggest reagents that will convert 19 into 23 .

Okay, so I have to answer the following questions and the first one where we are reacting. See the finan? So a benzene ring with a two carbon chain. And on carbon one, we have the key tone. So we're reacting with Yes, to the carbon adjacent to the carbon. Neil isn't as the alpha carbon, and it has alpha hydrogen. So whenever you reacted with a base, it's going to grab a ha Jin and eventually form a needle. Double bonds can form their. This bond is gonna break surrounding of this structure. We have the Alcock side island double bond right there, Every acting with this, this bond reforms, this becomes more reactive. Do we now have an addition? Products? And if we repeat this twice with the rest of the alpha hydrogen czar here, So let's see the base grabs both these hot regions. Is he doing this twice? We eventually get to structure. This is our, by the way, love ci three, which is better leaving group than the CH three. So again reacting with base, it's going to attack the carbon carbon, the sun get the ark oxide. We're just going to regenerate itself here is the addition of the Ohh. You still the ci three? It's going to expel this group as opposed to the O. H. So get this structure plus ch Sorry. Plus, um see, I three minus So it's going to dip originate accurate. And this is the products. So the ACC oxide ion with C h I threw. This is B is the yellow solid Say? Mm hmm. I mean, this is, um structure 21 zipper be We have to, um, through the mechanism for br two reacting with hydrogen or an acid. Do you get the structure? So yeah, we start. We're starting with the seat of finan, so it's gonna be similar to what we did in a mechanism, but this time it's under acidic conditions. So instead of the the base deep originating the metal, the oxygen on the carbonnel group is going to grab a person from an acid for use. Um um acetic acid. So ethanol kassid. It's going to deeper near the acid. Get the alc oxide ion. So this is going to be Oregon. It's group is that that's a hydrogen positive charge. And then we are Get this Cox Ri on So this is going to Deep Creek near the alpha oxygen Preakness bond. Get this and and then have the be the structure. So it's going to reform this bond and double bond here. It's a So we get. Show me. Do this. So once this bond reforms here, it's going to cause this double bond to attack a Peruvian, expelling that group or breaking the bond right there. So we got the addition of Permian. The final step is forward to grab the hydrogen from carbon You. So you're gonna get same same edition products, just a different mechanism, if for from for C, whereas to convert 19 to 23 again, starting with the seat. Afternoon. So we have this structure. So whenever you have this arrangement of Akita next channel keen, it's usually characteristic of an Aldo reaction. Do you have an eagle reacting with either an alcoholic or cartoon? In this case, you have a key town which will become a um and it'll Ah, so we have two carbons here and three over here. So if we reacted with formaldehyde, we only need one more carbon. Well, let's get the anal first. So this is going to become the evil. If you'd reacted with a strong base, like sodium with oxide, it's going to deep originate the Alpha Hodgins again and to be the same mechanism. So eventually, the alc oxide ion Obama their spawn breaks. Just be Oregon. Get this, um, Aquino in here and then reacting with. So, so far, we have one with two carbons we need We need one more. So let's react it with from, uh, from al to hide. I just want carbon. This bond trying to break this double bond is going to attack the carb meal. Look at this key. Turn again, the carbon, and then we have the primary alcohol. So if we do, actually hold on, Mr. Draw this. Do some hydrogen, Sir Cox on iron, every act of water. It's going to depart in it. You get the structure. So if we reacted with either a base and he or an acid and heat, it's gonna give us the Alpha Beta unsaturated kita Pelosi. So you get the vaccine. I am. Still have Hodgins are here. So you replace the r with a benzene ring. Yet? Products from the Aldo reaction

Mhm. Yeah, yeah.

This arrest. Answer the following questions and we're starting with Ben's Aldo Hood. So in the first one, we're reacting Benzo to hide with Ethel magnesium bromide to the Green Yard. Regent, This carbon is nuclear folk. It's going to attack the carbon carbon You were the cue tune eventually to an alcohol. So we're gonna get It's also going to add on whatever was attached to magnesium bromide onto the carbon that was attacked. So the addition of an Apple group so reacting with Kermit Acid, which is a strong oxidizing agent, it's going to convert it into a key tune. If we reacted chronic acid with a primary alcohol, it was converted to carve oxalic acid. But here we have a secondary alcohol, so it doesn't matter what we reacted with. They're finally with, um, metal magnesium bromide. Check the carbon carbon. We get the addition of a metal. So for B, we have to create the structure from Ben's out a hood. So whenever you were at the kitten with either ethane, one to file or ethane one to dial the dial meaning to alcohols like ethylene glycol, it's going to replace the the key tune with these two groups the two alcohols and drop the hydrogen. But in the case of F A n one to file, that's going to replace the kitchen with the two sulfur atoms and drop the hydrogen. We're going to keep the two carbon chain between them. So reacting with ethylene once you thought all will give us that? Yeah, and they're reacting with Raney nickel. We'll get rid of it. So you're still a metal order. Welcome back to it. So it's a good way to get rid of key to I mean, protecting groups like ethylene glycol for ketones by reacting with Raney Nickel. Then lastly were asked to create converts structure to into 12. And we're starting with Ben Zadi in. So you want to create this? So whenever you have this rearrangement of this arrangement of key tune next to an AL Keen, it's pretty characteristic of an audible reaction. So the a l implying within Al to hide are reacting with alcohol, and the ol is with an alcohol or I am. You had alcohol. So you're starting with Ben's outta high. We want to get we want to get the structure. So in all the reaction. We react a key tune with a strong basic Sorry myth oxide. So let's say we had So we're starting with one. We're starting with one carbon. We need two more and this three carbon chain. It has to be attached to a benzene ring toe. So what's at the benzene ring? And then we need to more carbons. And the older reactions only work with key tunes. So let's get that. If you have reacted with soda myth oxide, it's going to deeper donate the the alpha hydrogen, which is the the hydrogen on the carbon that's adjacent to the Carbondale Carbon. So grab a hydrogen and we'll get this rearrangement form a bond right there. Still, bond will break. This is gonna be RV. It's with the AC oxide ion double bond right there. And now we can react this with Benzarti, which we started with this double bond reforms and this double bond tax, the carbon carbon. This is gonna be our A You're the key tune, then the We have the three carbon chain now. So this is 12 three. I mean, hold on. Um, yeah. So this is one, two, three to the carbon carbon number one until we have just now Kane in the three has the alcohol. Mm hmm. This is done over water two. Turn the Alcock side back into an alcohol. Show the mechanism. So if we react this with a base or an acid with heat, it's going to turn the alcohol into anarchy in in the most stable position and regenerate the key tune. So if we reacted with a base, it's gonna deeper into the alpha option again. A double bond form right there. The spinal break. So we have the Alcock said ion again. You stole the alcohol double bond right there. So this bond reforms. This adds right there. This group leaves and we get the key. Turn back. We have double bond right there. So if we redraw the benzene rings for our d n r a, we have the products


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