5

6.52 In Chapter 18 we will learn about the hydrolysis of acetals to aldehydes and ketones: Four of the seven steps in the mechanism for this process are shown in th...

Question

6.52 In Chapter 18 we will learn about the hydrolysis of acetals to aldehydes and ketones: Four of the seven steps in the mechanism for this process are shown in the conversion of acetal to hemiacetal E::0:H-OSO3HOHHzoHSO;-acetalHSOa"CH;OHhemiacetal HzSO4Add curved arrows for each step_ Draw another resonance structure for C Identify the nucleophile and electrophile in Step [3] Which steps are Bronsted-Lowry acid-base reactions?

6.52 In Chapter 18 we will learn about the hydrolysis of acetals to aldehydes and ketones: Four of the seven steps in the mechanism for this process are shown in the conversion of acetal to hemiacetal E: :0: H-OSO3H OH Hzo HSO;- acetal HSOa" CH;OH hemiacetal HzSO4 Add curved arrows for each step_ Draw another resonance structure for C Identify the nucleophile and electrophile in Step [3] Which steps are Bronsted-Lowry acid-base reactions?



Answers

As we will see in Chapter $16,$ the carbonyl group of aldehydes and ketones reacts with water to form a compound called a hydrate. The hydration of a carbonyl group is catalyzed by acid. Formaldehyde, for example, reacts as shown below. When dissolved in water, formaldehyde exists almost entirely as its hydrate. This aqueous solution is given the name formalin. The mechanism for this acid-catalyzed hydration is similar to the mechanism for the acid-catalyzed hydration of an alkene to give an alcohol and occurs by the following three steps. Step 1: Add a proton. Step 2: Make a new covalent bond between an electrophile (an electron-seeking species) and a nucleophile (an electron-donating species). Step 3: Take a proton away. Write an equation for each step and show by the use of curved arrows how each of these steps occurs. Show all bond-forming steps and bond-breaking steps.

Hi. In this video, we're going to be going over a carbon. You'll chemistry specifically how we convert a compound with a carbon steel group to a hydrate. So these creations are very common. But before I begin, let me first go over what a carbon steel group it really is. So a carbon heel is a carbon that is double bonded to an oxygen. The important thing we have to remember is because of the difference in electro negativity. Is oxygen being a lot more of electro negative than carbon? We're going to have a intrinsic polarity in which carbon is partially positive, whereas oxygen is partially negative because it holds onto these electrons tighter and it hogs them. And so, in light of this knowledge, let's go over this reaction. So I'm converting formaldehyde, which is the most simple out to hide to its hydrate in the presence of water as well as an acid catalyst. So this reaction occurs in three main steps. First, we're going to protein eight, the carbon Neil oxygen. Then we're going to form a Covalin bond between a nuclear file as well as an electro filic region within this formaldehyde and then we're going to D protein eight water at the end. And this will be more clear as I draw this mechanism. So first, let's draw formaldehyde again. So in the first step, right in the first step, we have the acid catalyst. We have the acid catalyst and this carbon. Neil, this, uh, Carbonell oxygen is going to It's going to attack this hydrogen. And then these two electrons are going to be kicked off and put on this oxygen, uh, of this acid right here forming water. So what we have formed is this intermediate in which oxygen has a formal charge of plus wind. I realize here, very importantly, is that this carbon right here of this Carbonell group is still partially positive, making it the electro electro Filic region, right? It wants electrons because it's partially positive. So what ends up happening is we have water it here, which has which is going to be our nuclear file. It's a weak nuclear file, but that's going to attack this electro Philip carbon kicking these two electrons off onto oxygen so that oxygen can routine. It's formal charge of zero. And then we have this lovely water group as well as the two hydrogen. So we just formed a Covalin bond right right here, right here. Because of the reaction between our nuclear file water and the Electra Filic carbon region right here. And so in our last step, all we have to do is de protein. Eight is to de Protein eight. This water group, such that, uh, such that oxygen can then have a formal charge of zero. How we do that is water is going to then the protein eight, this water group right here and then what we're left with is formal in as we saw earlier. And then we also remake our acid as well. So that is the mechanism for this reaction. And I hope that this made a made this reaction more clear, as well as give you a better understanding of Carbondale chemistry.

He has in this question were given to reactions. We're in part A. We have the reaction between an out of hide and a seed allied I on forming a new alcohol and were also given the reaction between, um a sulfur, um, alcohol allied along this alcohol light is going through a sickle ization, and we're asked Teoh denote the movement of electrons with curved arrows. So let's go ahead and get started. So in part A, we have this, um, reaction where we're going to say this a seed Allied Ion is going to be our nuclear file since it has ah, lot of electron rich areas. And this out of Hyde is going to be our Electra file. So we know that, um, nuclear fouls attack electric files. So this, um, carbon right here or the electrons on the carbon are going to attack this carbon here and form a bond. And when we form a bond, we want to move the electrons that are, um, surrounding this carbon to maintain the octet. So I'm gonna move these electrons to this oxygen here. Since this oxygen can easily handle some negative charged electrons because of its electron negativity. So when we do that, we get this product right here Where the, um ah, satellite ion is bonded now to our carbon, and our oxygen has a negative charge. But we want this oxygen to remain stable with a pot or no charge and that target zero. So what we're going to do, we're gonna deep protein 81 of the water molecules that are in the solution. So to do that, we take one of the electrons here, and we're going to abstract a hydrogen from this. And this hydrogen ens bond is now going to break its electrons or break its bond to move its electrons to the hydrogen or the oxygen. Excuse me on this water. So when we do that, we formed this water molecule or this hydroxy molecule here for me and alcohol. And we're left with that, um, negatively charged ah hydroxy group here. And this is Thea movement of electrons for this reaction. So, in part B, we had the sickle civilization reaction of this compound. So when we do this, we want to take are leaving group, which is going to be bro Ming. In this case, we're gonna take its electrons forming its bond and put it on our broening, Adam. And since this sulphur is negative, this carbon is gonna be positive since it lost its electrons from the bond here. So it's going to come around and now bond to that carbon forming this cyclic shape and our bro Ming leaving group as a side product. So those are two reactions and the movement of electrons for

This is the answer to Chapter 20. Problem number 51 from the McMurray Organic chemistry textbook. Ah, this problem asks us to write a mechanism for acid catalyzed, uh, night trial, hydraulic sis. Um, it asks us to review the mechanism of the base catalyzed Nitra hydraulics, iss. Ah, and then to write the mechanism for the acid catalyzed hide your all icis. Okay. It also tells us, um, that, uh, the first step is gonna be pro nation of the nitrogen. Adam on, then That's gonna be followed by nuclear filling condition off water. Okay, so obviously, that's where we should start. So the first step is the problem says it's going pro nation of the nitrogen atom. Okay, so at this point, um, we're gonna have a positive charge on the nitrogen. Um, And then, as the problem says, the next step is going to be addition of a water molecule. So that is going to look like this. Ah, One of these bonds here and the triple bond will break, and those electrons will revert to the nitrogen. Okay, the next step eyes going to be a proton transfer. Um, and so ah, we can just um, we can just right Proton transfer. Okay, so that'll get us to this point. Um, from here, uh, one of these lone pairs of electrons will add in here. One of these bonds will break. And so as you can see, what we're working towards here is formation of a my ah. And so the last step that's going to have to happen to make that possible is gonna be deep protein nation. Um, and so we can just use another equivalent of water. Yes. I'm trying to write too high up eso We can just use another equivalent of water to make that happen. Okay. And so, uh, this point, we have formed a name, I Okay, um, so the second part of this mechanism, I'm gonna just redraw the a my down here just to give myself some space. Uh, not really. Any point trying toe crowd everything in s. So we have are a mine that we made. Um, looks like this. Okay. Uh, and so, um, Teoh, kick off this second part of the mechanism, it's again going to begin with a protein nation, which makes sense, because, remember, this is acid catalyzed. Um, whenever something's acid catalyzed. It's a pretty good bet that pro nation is a key. First step. So we protein ate the A mine in our oxygen. She puts us right here. The next thing that's going to happen eyes going to be addition of another water molecule, we can draw that below. So we now have Ah, Tetra. He'd roll intermediate here. Okay, Um, so, uh, the next thing that's going to happen, um, is going to be, um, another proton transfer. So just as we did above, we can just right proton transfer. Okay, Um and so now, of course, are nitrogen is gonna have a positive charge on it. Um, I suppose that I should have included the lone pair on the nitrogen. Ah, in these 1st 3 structures. So obviously it's it's gone now, in the fourth structure of since the nitrogen has a positive charge. Ah. And so the next thing that's going to happen is gonna be one of the lone pairs on this oxygen is gonna add in here to form a double bond. And that is going to kick out this ammonia. And so now you can see our carb oxalic acid is taking shape. So, actually, I'm going Teoh have the hydrogen pointing over here just cause there's a little more room that way. So we have a lone pair and a positive charge here. Two lone pairs here. Um and so the last thing that needs to happen to complete this mechanism is just gonna be deep protein nation. Um, and so that can actually be accomplished by, ah, the ammonia that we just made and released. So those electrons from the oxygen hydrogen bond, we'll go to the oxygen. Uh, and so we have made our carb oxalic acid. Just put the lone pairs in. Okay, there we go. So there's the acid catalyzed No trial, hydraulics, this mechanism. I drew it in two parts. Um, both parts rely on a first step being pro nation, followed by attack of water molecule. Um, and and then they proceed from there. Actually, both also followed by then a proton transfer. Um, yeah. Okay. S So that is the answer to Chapter 20. Problem number 51

In this question. We were asked to identify the Electra file and nuclear file in each step and then draw curved arrows to show how the reaction is happening. So in the 1st 1 are Electra file is the thing that's being attacked. So that is going to be the carbon here. Um, and then the nuclear file is the thing that's attacking, which will be the bro mean? So if we draw a curved arrows to show what's happening here, roaming will come in and attack from the opposite side system on carbon. On the opposite side of that, our, um, transitions are intermediate is on because the pyramid Intermediate that we have with the bro mean is too big to allows coming from the same side. So it will come in from the opposite side, and it will tack you more substitute carbon, and then this will push off. Um, and we'll end up with that other bro Ming on the top. Um, so then, for the 2nd 1 our nuclear file is the thing that's attacking. So that's going to be the NH two. And our laughter file is what's being attacked. That will be the hydrogen on this all kind. So we draw those curved arrows again. The any issue will come in and grab the hydrogen. And, um, the electrons in this bond will go on to be carbon to make that lone pair. That makes it a carbon Ryan. And in the 3rd 1 um, again, our nuclear file is with doing the attacking. So that will be this carbon nine over here and our electric files. What's being attacked? That will be the carbon on the ethyl bromide. And if we draw those arrows are nuclear ill will come in and attack our Electra file. And then we will push this broening off as a leaving group and give it that well, in parable electrons to make it negative.


Similar Solved Questions

5 answers
Find the area of the region bounded by the graphs of the following equations6r + &1=3 and X=7Hnnuinalls
Find the area of the region bounded by the graphs of the following equations 6r + & 1=3 and X=7 Hnnuinalls...
5 answers
1. (25 points) Find the interval of convergence of the power serics
1. (25 points) Find the interval of convergence of the power serics...
5 answers
Use carbon dioxide'$ phase diagramSupercritical fluid71.0SolidLiquidCas56, 4| Temperatun ( C)At ! atmosphere and room temperature (25*C) would you expect solid carbon dioxide (at-100*CJto melt to the liquid phase, or sublime to the gas phase?2 Some industrial processes require carbon dioxide; stored in large tanks as a liquid , In terms of pressure, What must be true of the carbon dioxide in those tanks?
Use carbon dioxide'$ phase diagram Supercritical fluid 71.0 Solid Liquid Cas 56, 4| Temperatun ( C) At ! atmosphere and room temperature (25*C) would you expect solid carbon dioxide (at-100*CJto melt to the liquid phase, or sublime to the gas phase? 2 Some industrial processes require carbon di...
5 answers
Fin 4 tle representakbm 'd Lineay 64 Operatov detu Reflecton 4 Pe.n t ho Lmenusionak vechr Spa& wxtt rexpeet t d-axis. IL Sur pose T 6aq1J vechy 2 Spa& caroA fr~ f Ovlhogonal 6a)is Ii 0j", [o 13" 6 [z '5 [o 03" What Tl ~epresentahon tlu ] CileWha} LT & t Trau Ilj a+e null;' hes 6} tk Hllawi% [email protected]|Az[:9 - A3 !d F,a4 thc tLe rany Spac 44 Tle Laes 9 t ebore m14104 muli spalla 2
Fin 4 tle representakbm 'd Lineay 64 Operatov detu Reflecton 4 Pe.n t ho Lmenusionak vechr Spa& wxtt rexpeet t d-axis. IL Sur pose T 6aq1J vechy 2 Spa& caroA fr~ f Ovlhogonal 6a)is Ii 0j", [o 13" 6 [z '5 [o 03" What Tl ~epresentahon tlu ] Cile Wha} LT & t Trau Il...
5 answers
QUESTION 47given material has work function of 1.76 eV: White lignt with wavel engths over ange from 374,5nmto 714nm is incident on this material What is the maximum kinetic energy ofan ectron which can be ejected from tne material by this Ilght? (1 nm 1.71536349132176 ev '5594259012016 ev 1,09159813084112 ev 2.18319626168224 ev 0.77971295060080-
QUESTION 47 given material has work function of 1.76 eV: White lignt with wavel engths over ange from 374,5nmto 714nm is incident on this material What is the maximum kinetic energy ofan ectron which can be ejected from tne material by this Ilght? (1 nm 1.71536349132176 ev '5594259012016 ev 1,0...
5 answers
Homework: HW 18: Section 9.1 (part 1) score 0 ol 6 ptsHW Score: 27.5936, Acf?9 plsOuud Felp1.25Gun4 Pp Gttu aini €outnccd Fmotnn Oo Kdoknrtuub Ve-houtdemn Getetovontn etatdstbmst Hoinn|MamiiGAnaA CouyeOneieUuen(etusu
Homework: HW 18: Section 9.1 (part 1) score 0 ol 6 pts HW Score: 27.5936, Acf?9 pls Ouud Felp 1.25 Gun4 Pp Gttu aini €outnccd Fmotnn Oo Kdoknrtuub Ve-houtdemn Getetovontn etatdstbmst Hoinn| Mamii GAna A Couye On eie Uu en (etusu...
5 answers
For which of the following sparingly soluble salt, the solubility (S) and solubility produce (Ksp) are related by the expressions $mathrm{S}=(mathrm{Ksp} / 4)^{13}$ ?(a) $mathrm{BaSO}_{4}$(b) $mathrm{Ca}_{3}left(mathrm{PO}_{4}ight)_{2}$(c) $mathrm{Hg}_{2} mathrm{Cl}_{2}$(d) $mathrm{Ag}_{2} mathrm{PO}_{4}$
For which of the following sparingly soluble salt, the solubility (S) and solubility produce (Ksp) are related by the expressions $mathrm{S}=(mathrm{Ksp} / 4)^{13}$ ? (a) $mathrm{BaSO}_{4}$ (b) $mathrm{Ca}_{3}left(mathrm{PO}_{4} ight)_{2}$ (c) $mathrm{Hg}_{2} mathrm{Cl}_{2}$ (d) $mathrm{Ag}_{2} math...
5 answers
Determine the volume enclosed between the hemispherical surface ~ = f(t,y) = ~ = 0 plane by evaluating the double integral FRr f(z,y) dA polar coordinates Give an exact value_ V = [4 points]22 y2 and the
Determine the volume enclosed between the hemispherical surface ~ = f(t,y) = ~ = 0 plane by evaluating the double integral FRr f(z,y) dA polar coordinates Give an exact value_ V = [4 points] 22 y2 and the...
1 answers
The following table shows the closing price of the three major stock markets on March 29,2018 : egin{tabular}{lc} hline Stock Market & Closing Price \ Dow Jones Industrial & 24,103 \ NASDAQ & 7,063 \ S&P 500 & 2,641 \ hline end{tabular}
The following table shows the closing price of the three major stock markets on March 29,2018 : egin{tabular}{lc} hline Stock Market & Closing Price \ Dow Jones Industrial & 24,103 \ NASDAQ & 7,063 \ S&P 500 & 2,641 \ hline end{tabular}...
3 answers
4 The time (in minutes) that a customer spends with a bank employee to get serviced is distributed with the exponential distribution with parameter O= 2. For a given customer; what is the probability that he will spend less than 5 minutes with the bank employee to get serviced?
4 The time (in minutes) that a customer spends with a bank employee to get serviced is distributed with the exponential distribution with parameter O= 2. For a given customer; what is the probability that he will spend less than 5 minutes with the bank employee to get serviced?...
5 answers
The elevation of the platform is controlled by two identical mechanisms, only one of which is shown. A load of 1200 lb is applied to the mechanism shown. Knowing that the pin at $C$ can transmit only a horizontal force, determine $(a)$ the force in link $B E,(b)$ the components of the force exerted by the hydraulic cylinder on pin $H$.
The elevation of the platform is controlled by two identical mechanisms, only one of which is shown. A load of 1200 lb is applied to the mechanism shown. Knowing that the pin at $C$ can transmit only a horizontal force, determine $(a)$ the force in link $B E,(b)$ the components of the force exerted ...
5 answers
Draw F(x)= SSIt 2ldt on a scaled set of axes_
Draw F(x)= SSIt 2ldt on a scaled set of axes_...
5 answers
The function $f$ is one-to-one. (a) Find its inverse function $f^{-1}$ and check your answer. (b) Find the domain and the range of f and $f^{-1}$.$$f(x)= rac{2 x}{3 x-1}$$
The function $f$ is one-to-one. (a) Find its inverse function $f^{-1}$ and check your answer. (b) Find the domain and the range of f and $f^{-1}$. $$ f(x)=\frac{2 x}{3 x-1} $$...
5 answers
7t (#.# th2 ave ivP lution (4/ J =dayhdat(Fiox 2 exelc ( & 50+h)01
7t (#.# th2 ave ivP lution (4/ J = dayhdat( Fiox 2 exelc ( & 50+h) 01...
5 answers
Use (8.5) to show that the given functions are linearly independent.$$e^{i x}, e^{-i x}$$
Use (8.5) to show that the given functions are linearly independent. $$e^{i x}, e^{-i x}$$...
5 answers
2 dx Co 128 +1
2 dx Co 128 +1...
5 answers
Explain what a politician meant when she said. "The speed at which the downtown area will be redeveloped is a function of the number of low-interest loans made available to the property owners."
Explain what a politician meant when she said. "The speed at which the downtown area will be redeveloped is a function of the number of low-interest loans made available to the property owners."...
5 answers
Complete the following nuclear equations and name the type of radiation. (20 pts) 23Al + %He 3 3GP + Zx16N 5 Zx + 180
Complete the following nuclear equations and name the type of radiation. (20 pts) 23Al + %He 3 3GP + Zx 16N 5 Zx + 180...
5 answers
A farmer has 2400 feet of wire to build a rectangular or square pen that encloses the maximum area: If the farmer wants to place two (2) lines of wire on each side, the dimensions of the pen that generate the maximum area are:Select one: a. 600 ft * 1200 ftbThe correct answer is notc. 1200 ft * 1200 ftd. 300 ft * 600 fte 600 ft x 600 ft
A farmer has 2400 feet of wire to build a rectangular or square pen that encloses the maximum area: If the farmer wants to place two (2) lines of wire on each side, the dimensions of the pen that generate the maximum area are: Select one: a. 600 ft * 1200 ft b The correct answer is not c. 1200 ft * ...
5 answers
MentWshtia: 61.2128Consider the definite integral7.(25 22)1/4 dx.What is the substitution to use? give the one that is the most efficient:) du For this correct choice, dx(There can be more than one valid substitution;If we make this substitution, then the integral becomes of the formf(u) du. What are a b and f(u)?"76 = 37f(u) Finally; use this work to computeJo Tx (25 _ 22)1/4 dc Give the exact value:
ment Wshtia: 61.2128 Consider the definite integral 7.(25 22)1/4 dx. What is the substitution to use? give the one that is the most efficient:) du For this correct choice, dx (There can be more than one valid substitution; If we make this substitution, then the integral becomes of the form f(u) du. ...

-- 0.018651--