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Questions and Answers
What is an asymmetric carbon atom also known as?
What is an asymmetric carbon atom also known as?
All monosaccharides contain at least one asymmetric carbon atom.
All monosaccharides contain at least one asymmetric carbon atom.
False (B)
What is the convention for presenting linear monosaccharides in a way that makes their chiral centers easily visualized called?
What is the convention for presenting linear monosaccharides in a way that makes their chiral centers easily visualized called?
Fischer projection
In the Fischer projection, the stereochemistry of a monosaccharide is reported as ______ or ______ based on the position of the H and OH groups on the chiral carbon farthest from the aldehyde or ketone.
In the Fischer projection, the stereochemistry of a monosaccharide is reported as ______ or ______ based on the position of the H and OH groups on the chiral carbon farthest from the aldehyde or ketone.
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Which enantiomer of glyceraldehyde is typically found in nature?
Which enantiomer of glyceraldehyde is typically found in nature?
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The number of possible stereoisomers for a given monosaccharide is determined by the number of what?
The number of possible stereoisomers for a given monosaccharide is determined by the number of what?
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What is the name for the simplest aldose triose sugar?
What is the name for the simplest aldose triose sugar?
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Which statement is TRUE regarding D-glucose and D-mannose?
Which statement is TRUE regarding D-glucose and D-mannose?
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Emil Fischer was the first to propose the cyclic structure of glucose.
Emil Fischer was the first to propose the cyclic structure of glucose.
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What is the name given to the cyclic structure of monosaccharides, such as glucose?
What is the name given to the cyclic structure of monosaccharides, such as glucose?
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The cyclic structures of monosaccharides form due to an interaction between the carbonyl group and the hydroxyl group on carbon 5 and 4 for hexose and pentose sugars respectively.
The cyclic structures of monosaccharides form due to an interaction between the carbonyl group and the hydroxyl group on carbon 5 and 4 for hexose and pentose sugars respectively.
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What is the name given to the cyclic structure of monosaccharides that resemble the five-membered ring compound furan?
What is the name given to the cyclic structure of monosaccharides that resemble the five-membered ring compound furan?
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Aldofuranoses are more stable than aldopyranoses.
Aldofuranoses are more stable than aldopyranoses.
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Only aldoses with five or more carbon atoms can form pyranose rings.
Only aldoses with five or more carbon atoms can form pyranose rings.
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What is the name given to the convention used to show stereochemistry of cyclic structures in monosaccharides?
What is the name given to the convention used to show stereochemistry of cyclic structures in monosaccharides?
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What are anomers?
What are anomers?
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What is the process by which the α and β anomers of D-glucose interconvert in an aqueous solution called?
What is the process by which the α and β anomers of D-glucose interconvert in an aqueous solution called?
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What is the name given to the chiral carbon in a hemiacetal or hemiketal?
What is the name given to the chiral carbon in a hemiacetal or hemiketal?
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In an aqueous solution, β-D-glucopyranose is present in a higher concentration than α-D-glucopyranose.
In an aqueous solution, β-D-glucopyranose is present in a higher concentration than α-D-glucopyranose.
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Ketohexoses can only form pyranose rings.
Ketohexoses can only form pyranose rings.
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What is the name given to the ring form of a ketohexose, such as fructose?
What is the name given to the ring form of a ketohexose, such as fructose?
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D-fructose primarily exists in its pyranose ring form.
D-fructose primarily exists in its pyranose ring form.
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Flashcards
Isomer
Isomer
Compounds with the same structural formula but different arrangements.
Chiral Carbon
Chiral Carbon
A carbon atom bonded to four different functional groups.
Optically Active
Optically Active
Molecules that rotate plane-polarized light due to chiral centers.
Fischer Projection
Fischer Projection
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D and L Isomers
D and L Isomers
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Stereoisomers
Stereoisomers
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Epimer
Epimer
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Haworth Projection
Haworth Projection
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Aldose
Aldose
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Ketohexose
Ketohexose
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Pyranose Ring
Pyranose Ring
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Furanose Ring
Furanose Ring
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Anomer
Anomer
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Mutarotation
Mutarotation
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Stereochemistry
Stereochemistry
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Chiral Center
Chiral Center
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Carbohydrate
Carbohydrate
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Aldotetrose
Aldotetrose
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Aldopentose
Aldopentose
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Aldohexose
Aldohexose
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D-Ribose
D-Ribose
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Glucose
Glucose
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Anomeric Carbon
Anomeric Carbon
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Hemiketal
Hemiketal
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Hemiacetal
Hemiacetal
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Aqueous Solution
Aqueous Solution
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Study Notes
Carbohydrate Structure and Isomerism
- Isomers are compounds with the same chemical formula but different structural arrangements.
- Monosaccharides contain asymmetric (chiral) carbon atoms, leading to different spatial arrangements.
- A chiral carbon atom has four different functional groups bonded to it.
- Monosaccharides, except dihydroxyacetone, have chiral carbons and exist as optical isomers (D or L).
- The D-isomer is more common in naturally occurring sugars.
- The number of possible stereoisomers depends on the number of asymmetric carbons (2n).
- Glyceraldehyde, the simplest aldose triose, has two enantiomers.
- Aldotetroses have four stereoisomers; aldopentoses have eight, and aldohexoses have sixteen.
- Epimers are isomers differing in the configuration of only one carbon atom. Glucose and mannose are epimers at carbon 2.
Cyclic Structures
- Monosaccharides readily form cyclic structures in solution.
- These structures arise from the interaction of the aldehyde or ketone group with a hydroxyl group.
- Cyclic forms can be pyranose (six-membered) or furanose (five-membered) rings. Pyranose rings are more stable.
- The carbon atom involved in the ring formation (typically carbon 1) is now called the anomeric carbon.
- The anomeric carbon can exist in two configurations, α or β, which represent different spatial arrangements of the hydroxyl group.
- α and β anomers interconvert in solution by a process called mutarotation.
- The most abundant form of D-glucose in solution is the β-D-glucopyranose form.
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Description
This quiz covers the essential concepts of carbohydrate structure, isomerism, and stereoisomerism. It highlights the importance of chiral carbon atoms and their role in forming various isomers, including D and L configurations. Test your knowledge on the cyclic structures of monosaccharides and their classifications.
