Textbook Question
Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.
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Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 26, Problem 16
Using the Haworth projection, draw the furanose ring that would form between the C4 hydroxyl group and the aldehyde at C1 for the molecule shown.
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Identify the functional groups involved in the ring formation. The C1 has an aldehyde group (CHO), and the C4 has a hydroxyl group (OH).
Understand that the furanose ring is a five-membered ring structure. In this case, the ring will form between the C1 aldehyde and the C4 hydroxyl group.
To form the furanose ring, the oxygen from the C4 hydroxyl group will attack the carbonyl carbon of the C1 aldehyde, forming a hemiacetal linkage.
Draw the five-membered ring structure. Place the oxygen atom from the C4 hydroxyl group as part of the ring, and connect it to the C1 carbon, which now has an OH group as a result of the hemiacetal formation.
Complete the Haworth projection by arranging the remaining carbon atoms (C2, C3, and C5) around the ring. Ensure that the substituents (OH and CH2OH groups) are placed correctly according to their original stereochemistry in the linear form.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Haworth Projection
The Haworth projection is a way of representing cyclic sugars in a two-dimensional format that illustrates the cyclic structure of monosaccharides. It shows the orientation of the hydroxyl groups and other substituents around the ring, making it easier to visualize the three-dimensional conformation of the molecule. This representation is particularly useful for understanding the anomeric carbon and the formation of glycosidic bonds.
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Furanose Ring Structure
A furanose ring is a five-membered cyclic structure formed from a monosaccharide, typically when the hydroxyl group on the C₄ carbon reacts with the carbonyl group at C₁. This reaction results in the formation of a hemiacetal, which is a key feature in the chemistry of sugars. Understanding the furanose structure is essential for predicting the reactivity and properties of sugars in biological systems.
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Anomeric Carbon
The anomeric carbon is the carbon atom in a sugar that was originally part of the carbonyl group (aldehyde or ketone) before the sugar cyclizes. In the case of furanose formation, the anomeric carbon is C₁, and its configuration (alpha or beta) determines the properties of the sugar. This concept is crucial for understanding the stereochemistry of carbohydrates and their interactions in biochemical processes.
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Related Practice
Textbook Question
Which of the following molecule pairs are epimers?
(a)
(b)
(c)
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Textbook Question
Suggest a mechanism by which α-d-glucopyranose is converted to β-d-glucopyranose in base. [See Figure 27.18.]
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Textbook Question
Using the Haworth projection, draw the furanose ring that would form between the C5 hydroxyl group and the ketone at C2 for the molecule shown.
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Textbook Question
Draw the α- and β-anomers of d-talopyranose. [The structure of talose is in Figure 27.11.]
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Textbook Question
Suggest a mechanism by which α-d-glucopyranose is converted to β-d-glucopyranose in acid. [See Figure 27.18.]
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