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Ch.5 - Stereochemistry
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.5 - StereochemistryProblem 5
Chapter 5, Problem 5

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.a. (S)-propane-1,2-diolb. (R)-2-bromobutan-1-ol

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Identify the chiral centers in each compound. For (S)-propane-1,2-diol, the chiral center is at the second carbon. For (R)-2-bromobutan-1-ol, the chiral center is at the second carbon.
Draw the carbon chain vertically for each compound. For (S)-propane-1,2-diol, place the three carbon atoms in a vertical line. For (R)-2-bromobutan-1-ol, place the four carbon atoms in a vertical line.
Assign the substituents around the chiral center. For (S)-propane-1,2-diol, the second carbon has an OH group, an H atom, and a CH3 group. For (R)-2-bromobutan-1-ol, the second carbon has a Br atom, an H atom, and a CH3 group.
Arrange the substituents in the Fischer projection. For (S)-propane-1,2-diol, place the OH group on the left and the H atom on the right. For (R)-2-bromobutan-1-ol, place the Br atom on the right and the H atom on the left.
Ensure the correct stereochemistry. For (S)-propane-1,2-diol, verify that the configuration is S by checking the priority of the groups. For (R)-2-bromobutan-1-ol, verify that the configuration is R by checking the priority of the groups.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In these diagrams, vertical lines represent bonds that project behind the plane of the page, while horizontal lines represent bonds that project out towards the viewer. This format is especially helpful for visualizing the configuration of chiral centers in molecules.
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Chirality and Stereochemistry

Chirality refers to the geometric property of a molecule having non-superimposable mirror images, often due to the presence of asymmetric carbon atoms. Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Understanding the (R) and (S) nomenclature is crucial for accurately representing the stereochemistry of compounds in Fischer projections.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds, providing a unique name that conveys the structure of the molecule. It includes rules for identifying the longest carbon chain, numbering the carbon atoms, and designating functional groups. Proper application of IUPAC rules is essential for accurately drawing Fischer projections and ensuring clarity in communication among chemists.
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Related Practice
Textbook Question
For each of the compounds described by the following names,1. draw a three-dimensional representation.2. star (*) each chiral center.3. draw any planes of symmetry.4. draw any enantiomer.5. draw any diastereomers.6. label each structure you have drawn as chiral or achiral.c. (2R,3S)-2,3-dibromohexaned. (1R,2R)-1,2-dibromocyclohexane
Textbook Question
Which of the following pairs of compounds could be separated by recrystallization or distillation?b. and
Textbook Question
Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice.Build molecular models of any of these examples that seem difficult to youe. Chlorocyclohexanef. Cis-1,2-dichlorocyclobutane
Textbook Question
Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.c. (S)-1,2-dibromobutaned. (R)-butan-2-ol
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Textbook Question
Draw three-dimensional representations of the following compounds. Which have asymmetric carbon atoms? Which have no asymmetric carbons but are chiral anyway? Use your models for parts (a) through (d) and any others that seem unclear.c. ClHC═C═C(CH3)21-chloro-3-methylbuta-1,2-diened. ClHC═CH―CH═CH21-chlorobuta-1,3-diene
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Textbook Question
In Problem 5-3 , you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).e. Chlorocyclohexane f. Cis-1,2-dichlorocyclobutane
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