Textbook Question
The following compound has only one asymmetric center. Why then does it have four stereoisomers?
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Ch. 4 - Isomers: The Arrangement of Atoms in Space
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 5, Problem 39
a. Stereoisomers with two asymmetric centers are called ___ if the configuration of both asymmetric centers in one stereoisomer is the opposite of the configuration of the symmetric centers in the other stereoisomer.
b. Stereoisomers with two asymmetric centers are called ___ if the configuration of both asymmetric centers in one stereoisomer is the same as the configuration of the asymmetric centers in the other stereoisomer.
c. Stereoisomers with two asymmetric centers are called ___ if one of the asymmetric centers has the same configuration in both stereoisomers and the other asymmetric center has the opposite configuration in the two stereoisomers.
Verified step by step guidance1
Step 1: Understand the concept of stereoisomers. Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of atoms. They include enantiomers and diastereomers.
Step 2: For part (a), recall that enantiomers are stereoisomers where the configurations of all asymmetric centers are opposite between the two molecules. This means that if one stereoisomer has an R configuration at both centers, the other will have an S configuration at both centers.
Step 3: For part (b), note that identical stereoisomers occur when the configuration of all asymmetric centers in one stereoisomer is the same as the configuration of the asymmetric centers in the other stereoisomer. This means there is no difference in spatial arrangement.
Step 4: For part (c), understand that diastereomers are stereoisomers where at least one asymmetric center has the same configuration in both molecules, while the other asymmetric center has opposite configurations. This partial difference in spatial arrangement distinguishes diastereomers from enantiomers.
Step 5: Summarize the definitions: (a) enantiomers have opposite configurations at all asymmetric centers, (b) identical stereoisomers have the same configurations at all asymmetric centers, and (c) diastereomers have opposite configurations at one asymmetric center and the same configuration at the other.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereoisomers
Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This category includes enantiomers and diastereomers, which are crucial for understanding the behavior of molecules in biological systems and their interactions. The presence of asymmetric centers, or chiral centers, in a molecule leads to the formation of these stereoisomers.
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Determining when molecules are stereoisomers.
Chirality and Asymmetric Centers
Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of one or more asymmetric (chiral) centers. Each chiral center can exist in two configurations, typically designated as 'R' (rectus) or 'S' (sinister). The arrangement of these configurations determines the specific type of stereoisomerism exhibited by the molecule.
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Types of Stereoisomers
The two main types of stereoisomers are enantiomers and diastereomers. Enantiomers are stereoisomers that are mirror images of each other, while diastereomers are not. The question specifically addresses configurations of stereoisomers with two asymmetric centers, leading to classifications based on whether the centers are the same or opposite in configuration, which is essential for understanding their chemical properties and reactions.
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Related Practice
Textbook Question
Draw the stereoisomers of the following amino acids. Indicate pairs of enantiomers and pairs of diastereomers.
a.
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Textbook Question
(+)-Mandelic acid has a specific rotation of +158. What would be the observed specific rotation of each of the following mixtures?
c. 75% (-)-mandelic acid and 25% (+)-mandelic acid
1996
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Textbook Question
The stereoisomer of cholesterol found in nature is shown here.
a. How many asymmetric centers does cholesterol have?
b. What is the maximum number of stereoisomers that cholesterol can have?
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Textbook Question
1-Bromo-2-methylcyclopentane has four pairs of diastereomers. Draw the four pairs.
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Textbook Question
Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve (p. 115), has a specific rotation of +66. One commercial preparation results in a mixture with a 97% enantiomeric excess.
a. Does naproxen have the R or the S configuration?
b. What percent of each enantiomer is obtained from the commercial preparation?
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