Textbook Question
Which of the following are optically active?
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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 77a,b
Which of the following has an achiral stereoisomer?
a. 2,3-dichlorobutane
b. 2,3-dichloropentane
Verified step by step guidance1
Step 1: Understand the concept of chirality. A molecule is chiral if it has a non-superimposable mirror image, typically due to the presence of a carbon atom bonded to four different groups. An achiral molecule, on the other hand, has a plane of symmetry or a center of symmetry, making it superimposable on its mirror image.
Step 2: Analyze the structure of 2,3-dichlorobutane. Draw the molecule and identify the stereocenters (chiral carbons). In this case, carbons 2 and 3 are stereocenters because they are bonded to four different groups.
Step 3: Determine if 2,3-dichlorobutane can have an achiral stereoisomer. Check for the possibility of a meso compound, which is an achiral molecule despite having stereocenters. A meso compound occurs when the molecule has an internal plane of symmetry that makes it superimposable on its mirror image.
Step 4: Repeat the analysis for 2,3-dichloropentane. Draw the molecule, identify the stereocenters (carbons 2 and 3), and check for the presence of an internal plane of symmetry that could result in a meso compound.
Step 5: Compare the findings for both molecules. Determine which molecule has an achiral stereoisomer (a meso form) based on the presence of an internal plane of symmetry. This will help you identify the correct answer.
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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. A chiral molecule typically has at least one carbon atom bonded to four different substituents, resulting in two distinct enantiomers. Understanding chirality is crucial for identifying stereoisomers and their properties.
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What is chirality?
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, which are non-superimposable mirror images, and diastereomers, which are not mirror images. Recognizing the types of stereoisomers is essential for determining the presence of achiral forms.
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01:58Determining when molecules are stereoisomers.
Achirality
Achirality describes molecules that are superimposable on their mirror images, meaning they do not exhibit chirality. A molecule can be achiral if it has a plane of symmetry or if it lacks chiral centers. Identifying achiral stereoisomers is important in organic chemistry, as it influences the reactivity and properties of the compounds.
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Related Practice
Textbook Question
Which of the following has an achiral stereoisomer?
e. 1,3-dibromocyclobutane
f. 2,4-dibromopentane
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Textbook Question
Which of the following has an achiral stereoisomer?
i. 1,2-dimethylcyclopentane
j, 1,2-dimethylcyclobutane
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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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1
rank
Textbook Question
Name the following:
c.
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