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Biochemistry

Learn the toughest concepts covered in Biochemistry with step-by-step video tutorials and practice problems by world-class tutors

9. Carbohydrates

Hemiacetal vs. Hemiketal

1

concept

Hemiacetal vs. Hemiketal

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in this video, we're going to build up the knowledge to understand Hemi, A Settles and Hemi Kittles. Now, before we actually define Hemi, Aceto and Hemi Kettle, its first helpful to understand the reaction that results in civilization of mono sacha rides and so mono sack rides or sugars can sick lies via a nuclear Filic edition reaction that occurs between alcohol groups and the Carbonnel groups of Aldo hides or key tones. And so the alcohol's in this reaction are going to be new Cleo Filic, and so they will act as nuclear fouls, whereas the Carbonnel groups of the alga hides and key tones are electro filic, so they are going to act as the electro Files. And, of course, the an America Carbon is going to form upon sickle ization of the mono sacha ride. And so if we take a look at our example, we're going to see how alcohol's can react with both alga hides and key tones in ordered for a mono Sacha ride to Sick Lies. And so we'll confers, analyze our image over here on the left and notice at the top here we're just showing you this nuclear Filic edition reaction that occurs between the alcohol and alga hide. So notice here in orange What we have is the alcohol group And then of course, over here in green notice What we have is the alga hide group. And so, of course, the alcohol is going to be nuclear Filic. So it's electron density is going to attack the electro Filic Carbonnel group of the alga hide. And so, of course, we're not showing the full, full mechanism that results upon mono Sacha ride civilization. But this is the general idea that you guys should walk away with. Alcohols are nuclear filic alga hides are electro filic and so down below noticed that we're showing you a linear mono sacha ride and you can see that this linear mono sack Reid has an alga high group and it has the alcohol group here. Uh, that is, uh, needed for this nuclear Filic edition reaction to take place. And so this is going to be an internal reaction that occurs within the same molecule. And ultimately, this results in this pirate notes that we see over here when the C five carbon alcohol group interacts with the carbon eel group on the C one carbon. And so this is a pirate knows again because it contains a six member ring and notice that upon civilization of this mano Sacha ride, the An America carbon forms. And of course, the an American carbon we know from our previous lesson videos is the Onley carbon atom that's attached directly to two oxygen atoms, the ring oxygen and the oxygen of one of its alcohol Gers. Now, which will also notice, is that the animator Carbon before sickle ization used to be the carbon of the Carbonnel group. And so really, that's another way to think about the an America carbon. It's the carbon atom that used to be part of the Carbonnel Group. Now, over here in the right side box, notice that we have a very similar reaction. Except this time we have the alcohol group reacting with a key tone group instead of an alga hide. And so again, the only difference between the Al Haydn Ketone is that the key tone has the our group, whereas the Al head has the hydrogen. And so when we take a look at our linear mono sacha right here, notice that it contains both the key tone group and it contains the alcohol group. And so, uh, this reaction is able to take place internally within the same mono sacha, right? And that results in the sickle ization of the mono sack right to form this fear anos and recall. It's a few notes because it's a five member ID ring when the C five hydroxy group interacts with the C two key tone group. And, of course upon civilization, Theano, Mary carbon forms and theano Mary Carbon, you can see, is bound to two oxygen atoms directly. And it used to be the carbon that was part of the carbon eel group. And so now that we have a better understanding of the reaction that results in sickle ization of mono Sacha rides in our next video, we can distinguish between Hemi A Settle and Hemi Keitel. So I'll see you guys in that video
2

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Hemiacetal vs. Hemiketal

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So now that we're familiar with the reaction that allows mono sacha rides to sick lies in this video, we're going to focus on how civilization will form either a Hemi aceto or ah, Hemi Kettle. And so we already know from our last lesson video that the an America carbon will form upon mono, Sacha ride civilization. But what you may not have realized is that this an American carbon that forms will actually become part of a relatively unstable Hemi, a settle or Hemi kettle. Now the prefix Hemi is a prefix that means half and so literally Hemi a settle can be defined as half of an ass. It'll group. And so this is going to result from the reaction that we talked about in our last lesson video, which was an alcohol reacting with an alga hide group. And then, of course, ah, Hemi Key towel can be defined as half of a key towel group, and this is going to result from again the same reaction we talked about in our last lesson video, which is an alcohol group reacting with a key tone group. And so if we take a look at our example image down below, we can distinguish between Hemi, a settles and heavy key tales. And so, in this box here notice that the top half is showing the formation of a Hemi a settle and the bottom half of our image is showing the formation of a Hemi key towel. And so what you'll notice is that the Hemi a settle in Hemi kettle are resulting from the same exact reaction we talked about in our last lesson. Video, which is an alcohol group reacting with an alga high group, will form this Hemi aceto. And, of course, an alcohol group reacting with a key tone group will form the Hemi key towel. And so one thing that's interesting to note here is that the only difference between the alga hide and the key tone is actually the difference that we see here the hydrogen and the our group. And really, when you take a look at it, the only difference between the Hemi, a settle and the Hemi Keitel is the same exact hydrogen and our group, so notice that this hydrogen and this our group here is the Onley thing that makes the two different from each other And so what you'll notice is that the carbon atom that we have highlighted here in the middle is the an americ carbon. And again, the an American carbon is going to be part of either the Hemi Asset out or the Hemi kettle. And so, as we move forward through our course and get more practice looking at, heavy ass tells, we'll be able to easily distinguish them from each other. And really, it's just looking at the an America carbon and seeing if a hydrogen atom is attached or looking at the an American carbon and seeing if there's an additional our group attached. And so, just to be clear here, you can think of these are groups as the rest of the carbon ring or the rest of the sugar structure is. These are groups over here, and so again, we're focusing on looking at these, uh, in America carbons here and just seeing if there is, ah, hydrogen atom attached or if there is an our group attached. And so now that we see this, if we take a look at the previous image that we had up above from our previous lesson, video, which will notice is that the an America carbon that we have here is a Hemi ass. It'll because notice that it has the hydrogen, Adam, just like the Hemi a settle down here and then notice Over here on the right image. This is showing a Hemi key towel because going down, we have an R group. And so that is this our group that we have here and again as we move forward through our course will be able to apply the concepts that we've learned here. And you'll just get better and better at distinguishing between the Hemi ass tell and the Hemi Kitale. So this concludes our lesson on the difference between heavy ass telling him, Kitale, and I'll see you guys in our next video.
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Problem

Which of the following is a hemiketal?

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Problem

For monosaccharides to cyclize, an alcohol group must attack a carbonyl group within the same sugar.

A) Which carbon of the linear ketohexose shown below has the reactive carbonyl?

a) C1.

b) C2.

c) C3.

d) C4.

e) C5.

B) Upon cyclization, would a hemiacetal or hemiketal form?

5
Problem

Use the image of the following glucose molecule to answer the questions.

A) Upon cyclization, which of the red circled carbons becomes the anomeric carbon?

a) A. 

b) B. 

c) C. 

d) D. 

e) E.

B) Upon cyclization, would a hemiacetal or hemiketal form?

6
Problem

In the reaction shown below the compound on the far right is a:

Divider