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Compound A racemizes readily on heating to $100^{circ}$ but the rate is not affected by chloride ion and is the same in chloroform and acetic acid. Racemization in ...

Question

Compound A racemizes readily on heating to $100^{circ}$ but the rate is not affected by chloride ion and is the same in chloroform and acetic acid. Racemization in deuteroacetic acid $left(mathrm{CH}_{3} mathrm{CO}_{2} mathrm{D}ight)$ gives only undeuterated racemic $mathrm{A}$. Devise a mechanism for the reaction in accord with all the experimental facts.

Compound A racemizes readily on heating to $100^{circ}$ but the rate is not affected by chloride ion and is the same in chloroform and acetic acid. Racemization in deuteroacetic acid $left(mathrm{CH}_{3} mathrm{CO}_{2} mathrm{D} ight)$ gives only undeuterated racemic $mathrm{A}$. Devise a mechanism for the reaction in accord with all the experimental facts.



Answers

Two useful organic compounds that contain Cl atoms are drawn below. Vinyl chloride is the starting material used to prepare poly(vinyl chloride), a plastic used in insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic. Why is the C- Cl bond of vinyl chloride stronger than the C- Cl bond in chloroethane?

This is the answer to Chapter three. Problem number nine Fromthe Smith Organic Chemistry textbook. Ah, and in this problem, we're asked to consider acetic acid and it's confident. Base sodium acid T Um And so we're told that the melting point of acetic acid is 17 degrees C over the melting point of sodium acetate eyes 324 degrees C on were asked to account for this very wide difference. I'm and so again we should remember that a difference in melting point or boiling point is telling us, um, really about a difference in inter molecular forces s so obviously sodium acid Tate has much stronger into molecular forces. Then acetic acid does on. And so to figure out what the difference is, we can list the inter molecular forces in each eso acetic acid. I's gonna have Vander Wal's forces, um, as all molecules do. So Vander Wal's forces on there are carbon oxygen bonds. So we have staples. So we're gonna have a staple disciple interactions or die pulled diaper forces, huh? And then we also have a non oxygen with the hydrogen bound to it. So we're gonna have hydrogen bonding as Well, um, and so this seems like a pretty pretty strong into molecular forces. Um, for this molecule tohave. However, when we look at sodium acetate, we're going to have Vander Wal forces. Of course, we still have our disciple disciple interactions. Um, but we don't have hydrogen bonding. And this molecule, right, because the hydrogen on the oxygen is the hydrogen that that was given up as an acid. Um, but what we do have in sodium acid state is the negatively charged oxygen Ionic Lee bonding with the positively charged sodium ion. So we have an actual Ionic bonds taking place here. Um and so remember that there are only two real types of bonds, Covalin and Ionic. So we call hydrogen bonding hydrogen bonding. But we don't mean that it's actually forming bonds. Um, and so on. H Bond is a very strong inter molecular force, but it's not a bond on Ionic Bond is orders of magnitude stronger than hydrogen bond. Um, and so that and that alone is what accounts for this substantial difference in melting points. You're talking about a compound with an ionic bond, innit? Versus a compound without um, and so that that's what accounts for that difference. Ah, and that's the answer to Chapter three. Problem number nine

This is the answer to chapter 20 to problem number 19 Fromthe Smith Organic chemistry textbook. This problem says what product is formed when see Dick Acid is treated with this with each free agent. Ah, and so we have methods. I mean, for a metal mean and heat for B, um, and then for see metal mean and D C c um, okay. And so for a ah, if we just use methylene mean now, we're gonna do an acid base reaction. And so our product is going to be the ammonium car box lates salt. So we'll get our car box laid eye on you, and we'll get our protein ated method. I mean, um, so that would look like this. So ch three and hte three with a plus positive charge on the nitrogen. So the ammonium car box lates salt eso for B if we use metal mean again. But then we dehydrated with heat. In that case, we will actually get the a mind that we're looking for. So N h ch three. So we'll get our mettle a mine. Ah, and we'll also get water. Um, and then for see if we use us um, metal mean in D C C ah, Again, we're gonna get our A mine. Remember, D C C Works as a dehydrating re agent here. Eso Same product hasn't be here. Um, on. And then for the sake of completeness, we could also indicate Ah, that will get, um, our dye Psychlo hack. So, Excell, you re a product. Um, so why not? Okay. Uh, yeah. So we'll get the metal a mind that we were attempting to make. And we'll also get the dye Psychlo axel Yuria, which is the hydration product of D C C. Okay, uh, and so that's the answer to chapter 20 to problem number 19.

So let's calculate our event. How factor for this new solution? We're told that this new solution this solution has a new freezing point of minus three degrees Celsius. This is an adequate solution, which means our depression and freezing point is going to be three degrees Celsius because normal pure water freezes at zero degrees Celsius. So we have three degrees and let's plug in the rest of our equation. So three equals R van. How factor times are morality, which in this solution is 0.95 times our K of F constant, which is 1.86 degree Celsius per morality. So let's sell for I and we find that I our van how factor equals 1.697

So while fuel compounds have a higher melting and boiling point as compared to the hydrocarbons which are having the same molecule our weed let us consider acidic as it let me draw the structure. Representation. We have C H three see doubled one oxygen single board oxygen Partial hydrogen bonding Excision. Hi Georgian Partial excision wounding. We have carbon double point ch tweet. So let me write the partial charges. Positive, right? Wouldn't be partial negative partial negative on DDE passion positive. So the dotted line represents the formation off hydrogen bonding We're here on over here in ascetic acid, the negative polarized oxygen atom off carbonite group can have formation off hydrogen bonding with positively polarized hydrogen atom off which born off other molecules. In this state, there is more extensive association off car Bakley carb oxalic acid molecules with inter, more little of bonding. Because off this do tow alternation effect on dhe strong hydrogen bonding. It has a higher melting and boiling point. Asked similar molecular weight compound


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