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Questions and Answers
What is the characteristic of stereoisomers?
What is the characteristic of stereoisomers?
Which of the following is a characteristic of enantiomers?
Which of the following is a characteristic of enantiomers?
What is the difference between D-glucose and D-mannose?
What is the difference between D-glucose and D-mannose?
What is the relationship between D-galactose and D-mannose?
What is the relationship between D-galactose and D-mannose?
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What is an anomer?
What is an anomer?
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Which of the following is a characteristic of epimers?
Which of the following is a characteristic of epimers?
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What is the characteristic of diastereoisomers?
What is the characteristic of diastereoisomers?
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What is the relationship between D-glucose and D-galactose?
What is the relationship between D-glucose and D-galactose?
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What is the result of the C-1 in a ring structure becoming an asymmetric centre?
What is the result of the C-1 in a ring structure becoming an asymmetric centre?
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What is the primary factor that influences the optical activity of compounds?
What is the primary factor that influences the optical activity of compounds?
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What is the difference between the D and L enantiomers of glyceraldehyde?
What is the difference between the D and L enantiomers of glyceraldehyde?
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How does the L enantiomer of glyceraldehyde affect the plane of polarized light?
How does the L enantiomer of glyceraldehyde affect the plane of polarized light?
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What is the term for the isomers that differ in their optical activity?
What is the term for the isomers that differ in their optical activity?
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What is the designation of natural glucose in terms of its optical activity?
What is the designation of natural glucose in terms of its optical activity?
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What is the term for the ring structure that results from the C-1 in a ring structure becoming an asymmetric centre?
What is the term for the ring structure that results from the C-1 in a ring structure becoming an asymmetric centre?
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What is the primary difference between the alpha- and beta-configurations of a sugar?
What is the primary difference between the alpha- and beta-configurations of a sugar?
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What is the specific rotation of the α-D-glucose isomer?
What is the specific rotation of the α-D-glucose isomer?
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In which solvent will only the β-D-glucose crystallize?
In which solvent will only the β-D-glucose crystallize?
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What is the percentage of β-isomer in the solution if the rotation of the dissolved solution is 53°?
What is the percentage of β-isomer in the solution if the rotation of the dissolved solution is 53°?
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Why do α-D-glucose and β-D-glucose have different physical properties?
Why do α-D-glucose and β-D-glucose have different physical properties?
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What type of isomerism do α-D-glucose and β-D-glucose exhibit?
What type of isomerism do α-D-glucose and β-D-glucose exhibit?
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What is the total percentage of α- and β-isomers in the solution?
What is the total percentage of α- and β-isomers in the solution?
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In which solvent will only the α-D-glucose crystallize?
In which solvent will only the α-D-glucose crystallize?
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What is the percentage of α-isomer in the solution if the rotation of the dissolved solution is 53°?
What is the percentage of α-isomer in the solution if the rotation of the dissolved solution is 53°?
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What type of isomers are classified into two different classes?
What type of isomers are classified into two different classes?
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What is the difference between erythrose and erythulose?
What is the difference between erythrose and erythulose?
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What is the ring structure formed by hexoses?
What is the ring structure formed by hexoses?
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What is the shape of the 6-membered ring formed by hexoses?
What is the shape of the 6-membered ring formed by hexoses?
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What is the reaction that forms hemiacetals and hemiketals?
What is the reaction that forms hemiacetals and hemiketals?
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What is the type of isomerism seen in ribose and ribulose?
What is the type of isomerism seen in ribose and ribulose?
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What is the term for the isomers that have the same molecular formula and bond order, but differ in their three-dimensional arrangement of atoms?
What is the term for the isomers that have the same molecular formula and bond order, but differ in their three-dimensional arrangement of atoms?
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What is the type of ring structure formed by ketohexoses and aldopentoses?
What is the type of ring structure formed by ketohexoses and aldopentoses?
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What is the purpose of periodic acid (HIO4) in carbohydrate analysis?
What is the purpose of periodic acid (HIO4) in carbohydrate analysis?
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What happens to the carbon participating in the cleavage reaction during periodate oxidation?
What happens to the carbon participating in the cleavage reaction during periodate oxidation?
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What is the effect of a hemiacetal carbon involved in a glycosidic linkage on periodate oxidation?
What is the effect of a hemiacetal carbon involved in a glycosidic linkage on periodate oxidation?
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What is optical activity?
What is optical activity?
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What is specific rotation?
What is specific rotation?
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What type of compounds can be oxidized by periodic acid?
What type of compounds can be oxidized by periodic acid?
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What is the effect of methylation on the cleavage reaction?
What is the effect of methylation on the cleavage reaction?
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What is the type of reaction that occurs during periodate oxidation?
What is the type of reaction that occurs during periodate oxidation?
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Study Notes
Steroisomers
- Same structural formula but with different spatial configuration
- Enantiomers: four different atoms or groups of atoms are attached to an asymmetric carbon
- Example: D and L glyceraldehyde, which are mirror images of each other
- Epimers: isomers that differ due to the H and OH configuration of carbons 2, 3, or 4
- Example: D-glucose and D-mannose are epimers at C-2, and D-glucose and D-galactose are epimers at C-4
Diastereoisomers
- D-glucose and D-mannose are epimers at C-2, and D-glucose and D-galactose are epimers at C-4
- D-galactose and D-mannose are diastereoisomers, as they differ in more than one carbon
Anomers
- Result from cyclization, adding an additional asymmetric carbon
- The C-1 in a ring structure can become the asymmetric center of the ring, resulting in alpha- and beta-configurations of the sugar
Optical Isomerism
- The presence of asymmetric carbons or chirality influences the optical activity of compounds
- Example: D and L enantiomers of glyceraldehyde have identical properties, but differ in optical activity
- Optical activity is measured by the rotation of the plane of polarized light
- L rotates clockwise, while D rotates counter-clockwise
- Examples: D(+) glucose, D(-) fructose
Structural Isomerism
- Isomers with the same molecular formula but different structural or spatial arrangements
- Classified into two classes: structural isomers and optical isomers (stereoisomers)
- Examples: erythrose (aldose) and erythulose (ketose), ribose and ribulose, xylose and xylulose
Pyranose and Furanose Ring Structures
- Monosaccharides in solution do not exist in open-chain structures, but rather cyclize into rings
- Hexoses form 6-membered rings, while ketohexoses and aldopentoses form 5-membered rings
- Haworth structures are used to represent the ring structures
Haworth vs Chair Formation Structure
- The 6-membered ring is not planar, but rather exists in a chair formation
Optical Activity of Compounds
- A solution of glucose can have different physical properties depending on the percentage of α- and β-isomers
- The specific rotation of the β- and α-isomers can be used to calculate the percentage of each isomer in a solution
Dissacharides
- Natural carbohydrates usually contain more than one monosaccharide unit
- Periodic acid (HIO4) is used to cleave C-C bonds and analyze carbohydrates
Periodate Oxidation
- Periodic acid cleaves C-C bonds if both carbons have hydroxyl groups or if one carbon has a hydroxyl group adjacent to another carbon with an amino group, keto, or aldo oxygen
- Every cleavage results in an oxidation
- The carbon participating in the cleavage reaction is oxidized to the next level (e.g., alcohol to aldehyde, and aldehyde to carboxylic acid)
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Description
Learn about stereoisomers, including enantiomers and epimers, and diastereoisomers in organic chemistry. Understand the differences in spatial configuration and atom arrangement.
