Textbook Question
A molecule of the type shown is discussed in greater detail in Section 6.5.1. Although it contains at least one atom with four different groups attached, why is it not a chiral molecule?
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Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 5, Problem 12e
Identify the following molecules as chiral or achiral. If chiral, draw the nonsuperimposable mirror image and verify its nonsuperimposability.
(e) 
Verified step by step guidance1
Step 1: Analyze the molecular structure provided in the image. The molecule is a benzene ring with two substituents: one methyl group and one ethyl group attached to adjacent carbon atoms on the ring.
Step 2: Determine if the molecule has a plane of symmetry. A molecule is achiral if it has a plane of symmetry, meaning one half of the molecule is a mirror image of the other half.
Step 3: Observe the substituents on the benzene ring. The methyl and ethyl groups are positioned such that the molecule has a plane of symmetry passing through the benzene ring and the substituents. This symmetry indicates that the molecule is achiral.
Step 4: Since the molecule is achiral, it does not have nonsuperimposable mirror images. Chiral molecules lack symmetry and have stereocenters, which this molecule does not possess.
Step 5: Conclude that the molecule is achiral based on the analysis of symmetry and the absence of stereocenters.
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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 a carbon atom bonded to four different substituents, leading to two distinct forms known as enantiomers. Understanding chirality is crucial for determining the optical activity of compounds, which is important in fields like pharmaceuticals.
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What is chirality?
Nonsuperimposable Mirror Images
Nonsuperimposable mirror images are pairs of structures that cannot be aligned perfectly, even when rotated or flipped. This concept is central to chirality, as chiral molecules possess such mirror images, known as enantiomers. To verify nonsuperimposability, one can use models or drawings to demonstrate that the two forms cannot be made to coincide.
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Achirality
Achirality describes molecules that are superimposable on their mirror images, meaning they do not have a distinct left or right form. Achiral molecules often have a plane of symmetry or identical substituents around a central atom, which eliminates the possibility of forming enantiomers. Recognizing achiral structures is essential for distinguishing them from chiral ones in organic chemistry.
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Related Practice
Textbook Question
Identify the following molecules as chiral or achiral. If chiral, draw the nonsuperimposable mirror image and verify its nonsuperimposability.
(c)
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Textbook Question
For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.
(f)
Textbook Question
For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.
(e)
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Textbook Question
Identify the following molecules as chiral or achiral. If chiral, draw the nonsuperimposable mirror image and verify its nonsuperimposability.
(f)
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Textbook Question
For each of the following chiral molecules, obtain the enantiomer (i) by drawing the nonsuperimposable mirror image and (ii) by switching the spatial orientation at each asymmetric center. Confirm (possibly using models) that the structures you drew for (i) and (ii) are the same.
(b)