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Questions tagged [carbohydrates]

Carbohydrates are one of three classes of primary metabolites and thus natural products. They are polyhydroxylated hydrocarbons and their derivatives. Colloquially, they are known as sugars. This tag may be applied to all questions that concern carbohydrate species in solution, reaction mechanisms and structures.

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24 views

Reducing sugars and redox potential

I am wondering if reducing sugars are those that can act as reducing agents, and they act as such with Tollens and Fehling reaction, then what's the redox potential here? And is it a reversible ...
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Dextrose equivalent values (DE) of the most common sugars

What are the dextrose equivalent values (DE) of lactose, and other common sugars? Some data like the values for sucrose (0), maltodextrin (x<20), maltose (52), and glucose (100) can be found at ...
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225 views

Ring Flip of glucose

I have recently read about mutarotation of glucose specifically I am familiar with how cyclic structures like substituted cyclo-hexanes exist in an equilibrium of both their chair conformers. The ...
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95 views

Why does α-ᴅ-glucose form at a lower temperature than β-ᴅ-glucose?

β-ᴅ-glucose is more stable than its α-anomer due to the fact that all the −OH groups occupy the equatorial position. If this is the case, then why does α-ᴅ-glucose predominate at 30 °C while β-ᴅ-...
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75 views

Looking for a compound that when mixed with sugar will burn when a drop of water is added

Years ago, I watched a Johnny Carson episode where a guest on the show mixed a compound with ordinary table sugar and added a drop of water and the mixture burst into flames. I went and bought the ...
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70 views

D and L configuration of monosaccharides

I got this question in the last week's test from Organic Chemistry. I am a bit confused in assigning D and L configuration. Help me understand the topic of D and L configuration and help with this ...
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56 views

Phase of reaction between glucose and potassium cyanide to form amygdalin

I'm trying to write a detective-fiction novel, and I was wondering if potassium cyanide reacts with sugar only if the glucose for the amygdalin to form is dissolved in liquid or does it react even if ...
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681 views

Can sugars dissolve in liquid ammonia?

Can monosaccharides and disaccharides dissolve in liquid ammonia due to hydrogen bond formation? My rationale is that these sugars may be able to form hydrogen bond with ammonia ($\ce{NH3}$).
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106 views

Haworth structures of sucrose and lactose

The haworth structures of lactose and sucrose is My question is regarding the glyosidic linkage, in lactose it is represented as a zig zag and in sucrose it is a "V". What does that mean. ...
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236 views

What is the carbon content, by weight, of vegetable oil?

I have only a high school understanding of chemistry, so please bear with me and my ham-fisted question. I’m trying to understand the carbon content in vegetable oil. I get that various oils have ...
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45 views

What does per-O-acetylated glucopyranoside mean? [closed]

What does per-O-acetylated glucopyranoside mean? Can you please break down the roots?
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472 views

Pyranose v/s Furanose form of Glucose and Fructose

According to my textbook (Class 12 NCERT Chemistry): Fructose also exists in two cyclic forms which are obtained by the addition of —OH at C5 to the C = O group. The ring, thus formed is a five ...
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0answers
110 views

Can I extract solid sugar from any fruit juice at home?

The goal here is to isolate the sugar from all other compounds in the juice. In this case, I'm using apple juice and grape juice. The sugar does not need to be edible, as it is being used to make r-...
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Carbohydrate Chemistry for Candy Making

I am trying to understand the different behaviors of sugar syrups when it comes to candy making. Specifically, maple syrup vs molasses. In making maple candy, pure maple syrup is heated to soft ball ...
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Glucose and related aldohexoses are interconvertible with a little base. Does anybody know how much of each sugar is present at equilibrium?

If you add NaOH to D-glucose in water, a mixture of almost all aldohexoses will arise over time, including mannose and fructose. I wonder how much of each will be present and what could explain the ...
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407 views

Reaction of glucose acetal with acetic anhydride

The following problem was asked in JEE Mains 2020 (Sept 2, Shift 1), Consider the following reactions: $\ce{ (i) Glucose + ROH ->[dry HCl] Acetal ->[$x$ eq. of (CH3CO)2O] acetyl derivative }$ $\...
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1answer
108 views

Sucrose skeletal formula - missing Carbon and Hydrogen [duplicate]

I was reading the Wikipedia article about Sucrose, when I noticed that the skeletal formula was missing some $\ce{C}$ and $\ce{H}$ atoms. The chemical formula being $\ce{C12H22O11}$, I counted the $11$...
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865 views

Oxidation of hydroxyl groups of glucose

In all oxidation reactions of glucose, it seems that the aldehyde group alone gets oxidised and none of the hydroxyl groups. In one reaction with nitric acid, the aldehyde group and the terminal ...
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1answer
424 views

Do all reducing sugars show mutarotation?

Do all reducing sugars show mutarotation? I studied that for a sugar to be reducing it must possess a free aldehydo or keto group. Also, for a mutarotation interconversion between α- and β-forms of ...
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242 views

what is a sugar unit?

How a sugar unit is defined? I am trying to understand the structure of calicheamicins, and it is noted that They consist of an enediyne headpiece and a modified carbohydrate tail consisting of four ...
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246 views

Where does the beta notation come from in the alpha 1,2 beta glycosidic bond (in sucrose)? [duplicate]

I am confused as to where the beta is coming from (in the alpha-1,2-beta glycosidic bond in sucrose). I understand that the alpha is from the anomeric carbon of the glucose, but I don't see how the ...
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188 views

What is the chemical equation for a Maillard reaction? [closed]

I'm a 10th-grader in my first year of chemistry. We have an assignment to make a brochure about a certain reaction, and I'm studying Maillard reactions. Does anyone know the chemical equation ...
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1answer
749 views

Why are there two structures of L-Glucose in the Fischer projection?

We are told that L-Glucose is an enantiomer of D-Glucose, which would mean that they are mirror images of each other. But then we're also told that the L and D forms is determined by the spacial ...
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1answer
144 views

How is levulinic acid formed from sucrose? [closed]

I came across the following question: Sucrose on treatment with conc. $\ce {HCl}$ produces? The answer is given as levulinic acid. So how exactly does sucrose produce levulinic acid?
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221 views

Why glucose and other similar carbohydrates are oxidised fully by HIO4?

$\ce{HIO4_{(aq)}}$ requires the vicinal diols to have syn configuration, as it forms a cyclic periodate ester. But glucose does not have syn configuration at C3, and if you consider cyclic forms of ...
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1answer
959 views

Reactions which confirms the presence of cyclic structure of glucose [duplicate]

Are there any reactions that can be explained only on the basis of the cyclic structure of glucose rather than the open chain thus confirming its presence in the solution? Like a reaction that can ...
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80 views

Can a per-acetylated sugar anomerize?

So I have a question concerning a reaction mechanism for the reaction below. I know for certain that I get the alfa anomer, but I can't explain it. When I draw out the mechanism it doesn't make sense ...
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1answer
4k views

Oxidation of fructose with conc. HNO3

I recently studied carbohydrates. I was taught that fructose on oxidation with strong oxidizing agents like concentrated $\ce{HNO3}$ yields glycolic acid and tartaric acid along with trihydroxy ...
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1answer
642 views

Fischer's proof of the structure of glucose

To differentiate between Mannose and Glucose , Fischer developed a series of reactions to make the aldehyde group to alcohol and terminal alcohol to aldehyde. What was this series of reactions ? Even ...
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1answer
152 views

Haworth's research of glucose

Firstly haworth used CH3I/Ag2O with glucose which replaced 5 H by CH3 forming a acetal which locked the anomer and stopped the equilibirium of ring chain tautomerism. Under dilute acidic conditions ...
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Question on identification of a compound

Question: Multiple correct answers are possible My Approach: I just found structure Q for all options A, B, C and D for which I have uploaded the structures below with their corresponding options. ...
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1answer
208 views

What is the difference between the sugar in a fresh fruit and the sugar in a juice?

In this paper of the WHO, there is a distinction between intrinsic sugars, who are incorporated within the structure of intact fruit and vegetables, and sugars naturally present in fruit juices. (page ...
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2answers
671 views

What reagents can be used to distinguish pentose and hexose sugars?

I have been asked how I can differentiate D-glucose and D-xylose using the following reagents / reactions: Orcinol Benedict's test Ammoniacal silver nitrate $\ce{FeCl3}$ $\ce{C6H5SO2Cl}$,...
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1k views

Does cooling a potato change the nature of its carbohydrates?

A talk-show guest of Joe Rogan claimed that cooling a potato after cooking creates "resistant starch" that's better for human consumption https://www.youtube.com/watch?v=niwqfwA2Lb8 The claim is ...
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3k views

How long would it take for sucrose to undergo hydrolysis in boiling water?

I was reading the book Cocktail Codex and there was a snippet on avoiding boiling sugar and water to make simple syrup that made me a bit skeptical. Here it is: Heat also affects the molecular ...
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2answers
245 views

Will (3R,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one tautomerise in nitric acid?

The following question was sent to me .The question is " Which of the following is A ?" The given answer was a,b,c Background If both ends of an aldose chain are oxidized to carboxylic ...
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1answer
2k views

How are glycosidic linkages formed?

Consider glycosidic linkages in disaccharides. I know a condensation reaction occurs, with the loss of water. But which OH is lost? The O in the linkage belongs to which monosaccharide? Example: ...
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236 views

Fehling's solution - What is the shelf life of the unmixed A & B components?

If you prepare two separate solutions of Fehling's A and Fehling's B, what is the shelf life likely to be? Will the effectiveness of the solution diminish over time? The literature recommends ...
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1answer
344 views

Why doesn't open-chain glucose react with water readily in aqueous solution?

Though the exact number given varies from 0.02% to 3%, it's well agreed that glucose spends a very small percentage of its time in aqueous solution as a linear aldehyde. Glucose's overwhelming ...
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Why the use of MD simulations is less popular for the study of carbohydrates?

In classical all-atom MD simulations, the force fields for proteins, nucleic acids and lipids seem to be more well developed than carbohydrates. It seems to me that the use of MD simulations is not so ...
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2k views

How does existence of alpha and beta form of glucose prove that it exists as a cyclic structure

My book says that Glucose is found to exist in two different crystalline forms which are named as $\alpha$ and $\beta$. Next it says that This behaviour could not be explained by the open ...
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1answer
185 views

Nomenclature of carbohydrates

In the chapter on Biomolecules in my book, the following points are given regarding carbohydrates. Numbering the C-chain with consecutive rank The C-atom present in the aldehyde group of aldoses and ...
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91 views

What would happen if you burned paper with a laser, in a vacuum?

If you hit a piece of paper with a powerful laser inside a vacuum, what would happen? It sounds like it should not "burn" and have a flame spread over the paper, as there is, of course, no oxygen. ...
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Clarification in the mechanism for Molisch's test for glucose

Wikipedia says Molisch's test is a sensitive chemical test, named after Austrian botanist Hans Molisch, for the presence of carbohydrates, based on the dehydration of the carbohydrate by sulfuric ...
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How can a carbohyrate be hydrolysed?

Polysaccharides and disaccharides if they are neutral how do they undergo hydrolysis? When making a polysaccharide or a dissacharide dehydration synthesis occurs and why does it not get reversed ...
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2k views

Sugar: A molecule or crystal [closed]

Is sugar a molecule or a large crystalline structure composed of many molecules? What do we mean when we say sugar?
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9k views

Why does wood burn but not sugar?

Fundamentally, they're both carbohydrates, although the cellulose in wood is essentially polymerized glucose, which combined with its isomer fructose forms sucrose. So why does wood readily burn ...
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72 views

Can Molisch test be used to separate monosaccharides from polysaccharides?

Do the results of Molisch test on monosaccharides have any differences with when it's done to disaccharides or polysaccharides?
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Are Anomers Epimers?

epimers are the class of stereoisomers which differ along configuration at any carbon in a carbohydrate(generally), And anomers are the kind of stereo isomers that differ at the carbonylic carbon, ...
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1answer
124 views

Can sucralose form a syrup?

(Almost) Everyone is familiar with making simple syrup from table sugar and water. I was wondering if pure sucralose is also capable of forming a syrup. I wanted to do an experiment myself, but to ...