Textbook Question
In this attempt to convert the line angle drawing of d-erythrose (shown) to the Fischer projection (shown), by viewing it from a certain direction (shown), a mistake was made. What was the mistake?
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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 9b
Convert each line-angle drawing, using appropriate bond rotations, into a correct Fischer projection.
(b) 
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Identify the chiral centers in the line-angle drawing. In this aldopentose, there are three chiral centers, each carbon atom bonded to four different groups.
Determine the configuration (R or S) of each chiral center. This involves assigning priorities to the substituents based on atomic number and using the Cahn-Ingold-Prelog rules.
Visualize the molecule in a way that places the longest carbon chain vertically, with the most oxidized carbon (the aldehyde group) at the top. This is the standard orientation for Fischer projections.
Rotate the bonds around each chiral center to ensure that horizontal bonds in the Fischer projection represent bonds coming out of the plane (towards the viewer), while vertical bonds represent bonds going into the plane (away from the viewer).
Draw the Fischer projection by placing the substituents at each chiral center according to the bond rotations performed. Ensure that the stereochemistry matches the original line-angle drawing.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Line-Angle Drawing
Line-angle drawings, also known as skeletal structures, are a simplified way to represent organic molecules. In these diagrams, carbon atoms are implied at the ends and intersections of lines, and hydrogen atoms attached to carbons are not shown. This method is efficient for visualizing complex organic structures, such as sugars, by focusing on the connectivity of atoms.
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Fischer Projection
A Fischer projection is a two-dimensional representation of a three-dimensional organic molecule, often used for carbohydrates. In this projection, the molecule is oriented so that the carbon chain is vertical, with the most oxidized carbon at the top. Horizontal lines represent bonds projecting out of the plane towards the viewer, while vertical lines represent bonds going behind the plane.
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Bond Rotation
Bond rotation refers to the rotation around single bonds in a molecule, which can change the spatial arrangement of atoms without breaking any bonds. This concept is crucial when converting line-angle drawings to Fischer projections, as it allows for the correct orientation of substituents to match the projection's conventions, ensuring accurate representation of stereochemistry.
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Related Practice
Textbook Question
Draw Fischer projections of the following molecules.
(c)
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Textbook Question
Convert each line-angle drawing, using appropriate bond rotations, into a correct Fischer projection.
(c)
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Textbook Question
Convert each line-angle drawing, using appropriate bond rotations, into a correct Fischer projection.
(a)
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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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Textbook Question
Categorize the following monosaccharides as d or l.
(a)
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