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

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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Identify the chiral centers in each compound. For chlorocyclohexane, locate the carbon atom bonded to the chlorine atom. For cis-1,2-dichlorocyclobutane, identify the two carbon atoms each bonded to a chlorine atom.
Assign priorities to the substituents attached to each chiral center based on atomic number. The higher the atomic number, the higher the priority.
Orient the molecule so that the substituent with the lowest priority is pointing away from you (usually represented as a dashed line).
Determine the order of the remaining three substituents. If the order is clockwise, assign the configuration as (R). If the order is counterclockwise, assign the configuration as (S).
Repeat the process for each chiral center in the compounds to determine the configuration of each asymmetric carbon atom.

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Key Concepts

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

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. Chiral molecules typically contain one or more asymmetric carbon atoms, which are carbon atoms bonded to four different substituents. This property is crucial in organic chemistry as it affects the behavior of molecules in biological systems and their interactions with other chiral substances.
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R/S Nomenclature

The R/S nomenclature system is a method used to assign configurations to chiral centers in organic molecules. The 'R' (rectus) designation indicates a clockwise arrangement of priority substituents, while 'S' (sinister) indicates a counterclockwise arrangement. To determine the configuration, one must first assign priorities to the substituents based on atomic number and then observe the arrangement from the perspective of the lowest priority group.
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Cycloalkanes

Cycloalkanes are a class of hydrocarbons that contain carbon atoms arranged in a ring structure. They can exhibit chirality if the ring has substituents that create an asymmetric carbon atom. Understanding the structure and stereochemistry of cycloalkanes is essential for analyzing their reactivity and interactions, particularly when determining the R/S configuration of chiral centers.
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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
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
Make a model and draw a three-dimensional structure for each compound. Then draw the mirror image of your original structure and determine whether the mirror image is the same compound. Label each structure as being chiral or achiral, and label pairs of enantiomers.a. cis-1,2-dimethylcyclobutaneb. trans-1,2-dimethylcyclobutane
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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.a. ClHC═C═CHCl1,3-dichloropropadieneb. ClHC═C═CHCH31-chlorobuta-1,2-diene
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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.a. (S)-propane-1,2-diolb. (R)-2-bromobutan-1-ol
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