Textbook Question
Which of the following has an achiral stereoisomer?
i. 1,2-dimethylcyclopentane
j, 1,2-dimethylcyclobutane
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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 77e,f
Which of the following has an achiral stereoisomer?
e. 1,3-dibromocyclobutane
f. 2,4-dibromopentane
Verified step by step guidance1
Step 1: Understand the concept of chirality. A molecule is chiral if it has a non-superimposable mirror image, often due to the presence of a stereocenter (a carbon atom bonded to four different groups). An achiral molecule, on the other hand, either lacks stereocenters or has a plane of symmetry that makes its mirror image superimposable.
Step 2: Analyze the structure of 1,3-dibromocyclobutane. Draw the molecule and identify the positions of the bromine atoms on the cyclobutane ring. Check for the presence of stereocenters and determine if the molecule has a plane of symmetry or if it can exist as an achiral stereoisomer.
Step 3: Analyze the structure of 2,4-dibromopentane. Draw the molecule and identify the positions of the bromine atoms on the pentane chain. Check for the presence of stereocenters and determine if the molecule has a plane of symmetry or if it can exist as an achiral stereoisomer.
Step 4: Compare the findings for both molecules. Determine which molecule has an achiral stereoisomer by identifying if either molecule can adopt a conformation or configuration that results in a plane of symmetry or superimposable mirror images.
Step 5: Conclude which molecule (1,3-dibromocyclobutane or 2,4-dibromopentane) has an achiral stereoisomer based on the analysis of their structures and symmetry properties.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereoisomerism
Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of those atoms. This can lead to different properties and reactivities. Stereoisomers can be further classified into enantiomers and diastereomers, depending on their symmetry and the presence of chiral centers.
Chirality
Chirality is a property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. A chiral molecule typically has at least one carbon atom bonded to four different substituents, creating two distinct enantiomers. In contrast, achiral molecules possess a plane of symmetry and can be superimposed on their mirror images.
Achiral Stereoisomers
Achiral stereoisomers are stereoisomers that do not exhibit chirality, meaning they can be superimposed on their mirror images. These compounds may still have stereogenic centers but possess a symmetry that negates chirality. Identifying achiral stereoisomers is crucial in organic chemistry, especially when determining the optical activity of a compound.
Related Practice
Textbook Question
For many centuries, the Chinese have used extracts from a group of herbs known as ephedra to treat asthma. A compound named ephedrine has been isolated from these herbs and found to be a potent dilator of air passages in the lungs.
a. How many stereoisomers does ephedrine have?
b. The stereoisomer shown here is the one that is pharmacologically active. What is the configuration of each of the asymmetric centers?
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Textbook Question
Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?
a.
b.
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Textbook Question
Name the following:
c.
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Textbook Question
Citrate synthase, one of the enzymes in the series of enzyme-catalyzed reactions known as the citric acid cycle, catalyzes the synthesis of citric acid from oxaloacetic acid and acetyl-CoA. If the synthesis is carried out with acetyl-CoA that contains radioactive carbon (14C) in the indicated position, the isomer shown here is obtained.
a. Which stereoisomer of citric acid is synthesized: R or S?
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Textbook Question
Which of the following has an achiral stereoisomer?
a. 2,3-dichlorobutane
b. 2,3-dichloropentane
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