Textbook Question
Which of the following has an achiral stereoisomer?
e. 1,3-dibromocyclobutane
f. 2,4-dibromopentane
996
views
Ch. 4 - Isomers: The Arrangement of Atoms in Space
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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 77i,j
Which of the following has an achiral stereoisomer?
i. 1,2-dimethylcyclopentane
j, 1,2-dimethylcyclobutane
Verified step by step guidance1
Step 1: Understand the concept of chirality. A molecule is chiral if it cannot be superimposed on its mirror image. Achiral molecules, on the other hand, have a plane of symmetry or a center of symmetry, making them superimposable on their mirror image.
Step 2: Analyze the structure of 1,2-dimethylcyclopentane. Draw the molecule and consider the positions of the two methyl groups on the cyclopentane ring. Determine if there is a stereoisomer that has a plane of symmetry, which would make it achiral.
Step 3: Analyze the structure of 1,2-dimethylcyclobutane. Draw the molecule and consider the positions of the two methyl groups on the cyclobutane ring. Check if there is a stereoisomer with a plane of symmetry, indicating achirality.
Step 4: Compare the symmetry of the stereoisomers for both compounds. For 1,2-dimethylcyclopentane, assess whether the ring and substituents can adopt a conformation that results in a plane of symmetry. For 1,2-dimethylcyclobutane, evaluate the same criteria.
Step 5: Conclude which compound has an achiral stereoisomer based on the analysis of symmetry in their stereoisomers. Remember that achirality arises from the presence of symmetry in the molecule.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
3mWas this helpful?
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 chirality.
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.
Cycloalkanes
Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. The presence of substituents on the ring can lead to different stereoisomers. In the case of 1,2-dimethylcyclopentane and 1,2-dimethylcyclobutane, the arrangement of the methyl groups can influence whether the compound is chiral or achiral, depending on the symmetry of the molecule.
Related Practice
Textbook Question
Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?
a.
b.
2992
views
1
rank
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.
b. If the acetyl-CoA used in the synthesis contains 12C instead of 14C, will the product of the reaction be chiral or achiral?
1236
views
Textbook Question
Name the following:
c.
1424
views
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?
1616
views
Textbook Question
Which of the following has an achiral stereoisomer?
a. 2,3-dichlorobutane
b. 2,3-dichloropentane
1477
views
1
rank