Carbohydrate Chemistry

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Questions and Answers

What structural characteristic defines a ketose?

  • A carbonyl group at the end of the carbon chain.
  • A hydroxyl group above the plane of the sugar.
  • A carbonyl group anywhere other than the end of the carbon chain. (correct)
  • A branched structure with alpha 1-6 linkages.

How does the number of chiral carbons in a carbohydrate relate to the number of possible stereoisomers?

  • The number of stereoisomers is half the number of chiral carbons.
  • The number of stereoisomers is the square of the number of chiral carbons.
  • The number of stereoisomers is equal to the number of chiral carbons.
  • The number of stereoisomers is calculated as $2^n$, where n is the number of chiral carbons. (correct)

What is the primary structural difference between amylose and amylopectin?

  • Amylose is a branched polysaccharide, while amylopectin is linear.
  • Amylose is composed of fructose, while amylopectin is composed of glucose.
  • Amylose is a linear polysaccharide, while amylopectin contains alpha 1-6 branches. (correct)
  • Amylose contains beta 1-4 linkages, while amylopectin contains alpha 1-4 linkages.

What is the significance of non-reducing ends in glycogen?

<p>They allow for faster mobilization of glucose stores. (A)</p> Signup and view all the answers

Which of the following best describes mutarotation?

<p>The interconversion between alpha and beta anomers through a cyclic intermediate. (A)</p> Signup and view all the answers

What type of linkage is present in chitin and cellulose?

<p>Beta 1-4 linkages. (C)</p> Signup and view all the answers

Why can't humans digest beta 1-4 linkages found in cellulose?

<p>Because the required enzymes for breaking down beta 1-4 linkages are not produced in the human body. (A)</p> Signup and view all the answers

What is the distinguishing feature of an anomeric carbon?

<p>It's the carbon that becomes chiral during cyclization. (B)</p> Signup and view all the answers

During cyclization of a carbohydrate, what group attacks the carbonyl carbon?

<p>Hydroxyl group. (B)</p> Signup and view all the answers

If a carbohydrate has 3 chiral carbons, how many stereoisomers are possible?

<p>8 (B)</p> Signup and view all the answers

What is the role of starch in plants?

<p>Energy storage. (A)</p> Signup and view all the answers

In an aldose sugar, where is the carbonyl group located?

<p>At the end of the carbon chain. (C)</p> Signup and view all the answers

What characterizes epimers?

<p>They differ in configuration at a single chiral carbon. (B)</p> Signup and view all the answers

How are glucose residues linked together in amylopectin?

<p>Alpha 1-4 linkages with alpha 1-6 branch points. (C)</p> Signup and view all the answers

What determines whether a sugar is classified as a D-sugar or an L-sugar?

<p>The configuration of the chiral carbon most distant from the carbonyl carbon. (A)</p> Signup and view all the answers

How many residues between the alpha 1-6 branch points in amylopectin?

<p>25 (B)</p> Signup and view all the answers

Which of the following statements is true regarding alpha and beta isomers of glucose?

<p>In alpha isomers, the hydroxyl group is below the plane of the sugar. (D)</p> Signup and view all the answers

Which carbon atom is the anomeric carbon in ketoses?

<p>Carbon 2 (C)</p> Signup and view all the answers

Which polysaccharide has the highest frequency of branching?

<p>Glycogen (D)</p> Signup and view all the answers

What is a carbonyl carbon?

<p>Carbon with a double bonded oxygen. (C)</p> Signup and view all the answers

For every one carbon molecule in a carbohydrate, how many water molecules are associated with it?

<p>One (D)</p> Signup and view all the answers

Which of the following is a key characteristic that all carbohydrates share?

<p>They are all hydrates of carbon. (D)</p> Signup and view all the answers

What structural feature do both amylopectin and amylose share?

<p>They are both homopolysaccharides. (A)</p> Signup and view all the answers

What minimum number of carbon atoms are required for a carbohydrate to form cyclic structures?

<p>5 (B)</p> Signup and view all the answers

In which form of glucose does the hydroxyl group project above the plane of the sugar?

<p>Beta isomer (A)</p> Signup and view all the answers

What is always involved during cyclization?

<p>Carbonyl group (D)</p> Signup and view all the answers

What is the main chain and the branch point linkages in Glycogen?

<p>Alpha 1-4 main chain and alpha 1-6 branch points (A)</p> Signup and view all the answers

Carbohydrates have many?

<p>Chiral carbons (B)</p> Signup and view all the answers

How often is greater branching seen in glycogen?

<p>every 9 residues (B)</p> Signup and view all the answers

Flashcards

Carbohydrates

Hydrates of carbon

Carbonyl carbon

Carbon with double-bonded oxygen.

Epimers

Molecules differing in configuration at a single chiral carbon.

Ketose

Carbonyl group anywhere but at the end of the chain.

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Aldose

Carbonyl group at the end of the chain.

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Anomeric carbon

Carbon becomes chiral due to cyclization.

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Beta isomer

Hydroxyl group above the plane of the sugar.

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Alpha isomer

Hydroxyl group below the plane of the sugar.

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Mutarotation

Interconversion of alpha/beta forms via intermediate

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Starch

Energy storage in plants, made of amylopectin and amylose.

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Amylose

Homopolysaccharide of glucose with alpha 1-4 linkages.

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Amylopectin

Glucose residues with alpha 1-4 linkages and alpha 1-6 branch points.

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Glycogen

Branched polysaccharide with alpha 1-4 and alpha 1-6 linkages.

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Non-reducing ends

Allows faster mobilization of glucose stores.

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Chitin / Cellulose

Beta 1-4 linkages for elongated structures.

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Study Notes

Sugars

  • Carbohydrates are hydrates of carbon
  • For every carbon molecule, there is one water molecule associated with it
  • Carbohydrates have many chiral carbons
  • Stereoisomer amount is calculated as 2^n, where n is the number of chiral carbons
  • D or L sugar is based on the chiral carbon most distant from the carbonyl carbon
  • Carbonyl carbon is a carbon with a double-bonded oxygen
  • Epimers are two molecules differing in configuration at a single chiral carbon
  • Ketose: carbonyl group is located anywhere other than the end of the chain
  • Aldose: carbonyl group is located at the end of the chain
  • Cyclic structures form with carbohydrates containing 5 or more carbons
  • Cyclization happens when a hydroxyl group from within the sugar attacks the carbonyl carbon
  • Cyclization always involves a carbonyl group
  • Anomeric carbon is the carbon becoming chiral as a result of cyclization
  • In aldoses, carbon 1 is anomeric
  • In ketoses, carbon 2 is anomeric
  • Alpha isomers: hydroxyl group below the plane of the sugar
  • Beta isomers: hydroxyl group above the plane of the sugar
  • Mutarotation: interconversion of alpha and beta forms through a cyclic intermediate
  • Starch is used for energy storage within plants and is made of amylopectin and amylose
  • Both amylopectin and amylose are homopolysaccharides
  • Amylose is a linear homopolysaccharide of glucose joined by alpha 1-4 linkages
  • Amylopectin: glucose residues linked by alpha 1-4 linkages, with alpha 1-6 branch points about every 25 residues
  • Glycogen is a branched homopolysaccharide with alpha 1-4 main chain linkages and alpha 1-6 branch points
  • Glycogen has a greater frequency of branching, about every 9 residues, which creates more non-reducing ends
  • More non-reducing ends allow glucose stores to be mobilized faster
  • Chitin and cellulose utilize beta 1-4 linkages to form elongated structures
  • Humans cannot break down beta 1-4 linkages due to the lack of the necessary enzyme

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