Textbook Question
Without referring to the chapter, draw the chair conformations of
(d) N-acetylglucosamine, glucose with the C2 oxygen atom replaced by an acetylated amino group.
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Ch. 23 - Carbohydrates and Nucleic Acids
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 23, Problem 47b
Without referring to the chapter, draw the chair conformations of
(b) α-D-allopyranose (the C3 epimer of glucose).
Verified step by step guidance1
Understand the structure of α-D-allopyranose: It is a six-membered cyclic sugar (pyranose form) and the C3 epimer of glucose. This means the hydroxyl group (-OH) on the third carbon (C3) is inverted compared to α-D-glucopyranose.
Recall the rules for drawing chair conformations: In a chair conformation, substituents on the ring alternate between axial (perpendicular to the ring plane) and equatorial (parallel to the ring plane) positions. The α-anomer indicates that the anomeric hydroxyl group (-OH on C1) is in the axial position (down) for D-sugars.
Assign the stereochemistry for each carbon: Start with C1 (anomeric carbon) and place the -OH group in the axial position (down). For C2, place the -OH group in the equatorial position (up). For C3, since it is the epimer of glucose, place the -OH group in the axial position (down). Continue assigning the stereochemistry for C4 and C5 based on the D-configuration of the sugar.
Draw the chair conformation: Begin by sketching the six-membered chair structure. Place the substituents (hydroxyl groups and hydrogens) on each carbon according to the stereochemistry determined in the previous step. Ensure that the axial and equatorial positions alternate correctly.
Double-check the structure: Verify that the hydroxyl groups and hydrogens are placed correctly based on the α-anomer and the C3 epimer of glucose. Confirm that the chair conformation is drawn accurately with proper stereochemistry.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Chair Conformation
Chair conformation is a three-dimensional representation of cyclohexane and its derivatives, which minimizes steric strain and torsional strain. In this conformation, the carbon atoms are arranged in a staggered manner, resembling a chair, allowing for more stable interactions between substituents. Understanding chair conformations is crucial for predicting the stability and reactivity of cyclic compounds.
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Understanding what a conformer is.
Epimers
Epimers are a specific type of diastereomer that differ in configuration at only one stereogenic center. In the case of a-D-allopyranose, it is an epimer of glucose at the C3 position, meaning that while they share the same molecular formula and most stereocenters, they differ in the orientation of the hydroxyl group at that specific carbon. Recognizing epimers is essential for understanding carbohydrate chemistry and their biological roles.
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Pyranose Structure
Pyranose refers to a six-membered ring structure formed by the cyclization of monosaccharides, typically involving five carbon atoms and one oxygen atom. In the case of a-D-allopyranose, the ring structure is stabilized by the formation of an acetal linkage between the anomeric carbon and a hydroxyl group. Familiarity with pyranose structures is vital for analyzing the properties and reactions of sugars in organic chemistry.
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Related Practice
Textbook Question
Use Figure 23-3 (the D family of aldoses) to name the following aldoses.
(a) the C2 epimer of D-arabinose
(b) the C3 epimer of D-mannose
(c) the C3 epimer of D-threose
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Textbook Question
Glucose is the most abundant monosaccharide. From memory, draw glucose in
(a) the Fischer projection of the open chain.
(b) the most stable chair conformation of the most stable pyranose anomer.
(c) the Haworth projection of the most stable pyranose anomer.
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Textbook Question
Without referring to the chapter, draw the chair conformations of
(c) β-D-galactopyranose (the C4 epimer of glucose).
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Textbook Question
Without referring to the chapter, draw the chair conformations of
(a) β-D-mannopyranose (the C2 epimer of glucose).
Textbook Question
All of the rings of the four heterocyclic bases are aromatic. This is more apparent when the polar resonance forms of the amide groups are drawn, as is done for thymine here. Redraw the hydrogen-bonded guanine-cytosine and adenine-thymine pairs shown in Figure 23-24, using the polar resonance forms of the amides. Show how these forms help to explain why the hydrogen bonds involved in these pairings are particularly strong. Remember that a hydrogen bond arises between an electron-deficient hydrogen atom and an electron-rich pair of nonbonding electrons.
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