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Which of the following is the correet mechanism for the elimination reaction of 2-bromo- 2.3-dimethylbutane With methoxide?OCHa{OCHa_OCHaOCHa...

Question

Which of the following is the correet mechanism for the elimination reaction of 2-bromo- 2.3-dimethylbutane With methoxide?OCHa{OCHa_OCHaOCHa

Which of the following is the correet mechanism for the elimination reaction of 2-bromo- 2.3-dimethylbutane With methoxide? OCHa {OCHa_ OCHa OCHa



Answers

The reaction below is an example of: (A) esterification. (B) tautomerization. (C) elimination. (D) dehydration.

Part a here ancestor to draw the mechanism of this reaction. Eso here we're starting with a key tone and ending with it and alcohol on a now fully formed aromatic rings. And we're using h us before to get there. So this is a and this is an acid. So the first step is going to be Impersonating this, um, carbon oxygen here. So the first intermediate looks like this. Now, this is positive. Since its positive, we're gonna swing this double bond up onto that oxygen to give us an intermediate that looks like this and all the o. H is neutral. Um, and we have a positive charge on that carbon. And now that carbon is a carbon cat I in and can move around the ring. So thief first place that can move is if we push this bond over here. Um, that will give us an intermediate. That looks like this. Um, so this is not over here. And now my carbo Catalan is over there. And if I push it one more time to here now, it looks like this. And now it's right here. Now, this is a secondary carb okada and secondary little if we could make it tertiary Elik, if we did a metal shift, So that's what we're going to do. We're going to take this vessel group and move the electrons bonding the sea in the metal gear up to the sea and the ring over onto that one and said, Spec gives us now this carbo cat I am. Oops. Now it's over here, another's metal group on each one of those carbons. And then to get to our final product, all we're gonna do is an elimination. So a hydrogen on this carbon right here will, um, leave and the electrons there will push into there. So probably the county base of the issue s a four or some other nuclear file in the solution will grab that hydrogen off and the electrons in that Ohh that C h bond will push into there. And that will give us that double bond that we see right here. So that is the mechanism for that reaction and then part B as a strong a product of this reaction, which is going to happen by a similar mechanism. So again, the first thing that will happen is we'll protein ate that carbon oxygen and then push that double bond up onto the oxygen to make it an alcohol instead. Um And so then we'll have this structure. And now we have a car broke out, I And down there, um, And then, um, we'll move this total bond up there to move the car pool cattle and down. So now it looks like this. Um, And now my car broke. A tie in is over here. Um, and then we'll do that same metal shift with this metal group right here to make it a tertiary carbo Calyon instead, center. We have a methyl group on each one of these and the carbon cattiness here on the tertiary position and will have that same thing happened where we'll take an H, um, and that those electrons will go right into the middle there and form and that double bond. So then the final products will look like this. Now we have a double bond. Here are methyl groups are on opposite car on separate carbons now, and we have an alcohol on top. Left the product for part B

Yeah, The reaction ch two, Double one. See it. See 48 Hmm. Under basic condition. Oh, well h minus. Well, motor this mhm. See? And C h two c h two c w bulbul It is the mechanism for there is reaction involved. Obstruction off this problem language minus and followed by elimination. Oh, so I knew they only to give. See? It's too double bone sleep eggs C w going home, you know? Okay, they sign it. I own with this silly greater Okay, a text being in Meet me, But that's there when you get position. Tokyo CNN Keep yeah C s c N C h two See? That's minus. Yeah. C x four. Right. Which abstracts Welcome water and give separate. Leaving behind the boys minus the second reaction Also. Okay, it's in a very similar version. See, it's three CIA towards to you Any see escape feet? It's what? Well, it's right. See you then. C s double one c. It's too Oh, right. Oh, it's minus No, uh, in a similar passion Websites a brutal Who is minus mean? I start the brutal and vision is writing the elimination of Syrian. You will see extreme. See everyone Old. See, that's Did everyone see? It's too. Mm hmm. What? Hmm? On the sea and minus. Okay, Steve. And minus. Hm. A cake. And they're going to be perceiving toe. Get on it today, everyone. So that the product will see It's three. Seeing everyone for C H two C H, two c and okay. Uh, yeah.

We start a reaction with two brome. Oh, plantain. You can get different results, depending what we reacted with almost reaction. Our product will be pent one e. We have the same reacting but react. It's a different set, a compound we can get pent to in.

We just have another mechanism where we start with period Dean. And then we have an attack off. Ohh! Miners which shifts are electrons and gives our nitrogen and negative charge to hold on to on. Then we are able to lose a water molecule to generate this intermediate. And then we lose the hydroxide ion. This leaves us with our oxygen with a negative charge here, where we can now do some electron pushing in order to generate are Carbonell, which is our key tone head. And we know it's a key tone because we have own at the end of the names and now we have to period. I know while we still have that nitrogen in that cyclic ring. So this is the mechanism for the attack on the second position. This is our second position. We also have a partial positive charge on the fourth position and therefore we can also generate for period unknown


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