Textbook Question
Draw the most stable chair conformation for the following trisubstituted cyclohexane.
2
views
Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Mullins 1st EditionCh. 3 - Alkanes and Cycloalkanes: Properties and Conformational AnalysisProblem 40d
Mullins 1st EditionCh. 3 - Alkanes and Cycloalkanes: Properties and Conformational AnalysisProblem 40dChapter 2, Problem 40d
Given the following chair conformations, draw each in its planar form as if you were viewing it from above.
(d) 
Verified step by step guidance1
Identify the substituents on the chair conformation. In this case, the substituents are fluorine (F), hydrogen (H), and chlorine (Cl). Note their positions as axial or equatorial.
Understand the orientation of the chair conformation. The chair conformation alternates between axial and equatorial positions for substituents on adjacent carbons. Axial substituents point straight up or down, while equatorial substituents point slightly outward.
Translate the chair conformation into a planar form. To do this, draw a hexagon to represent the cyclohexane ring. Place the substituents on the appropriate carbons based on their axial or equatorial positions.
Ensure that the stereochemistry is preserved. For example, if a substituent is pointing up in the chair conformation, it should be drawn as a wedge in the planar form. If it is pointing down, it should be drawn as a dashed line.
Double-check the planar structure to confirm that all substituents are correctly positioned and the stereochemistry matches the original chair conformation.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Chair Conformation
The chair conformation is a three-dimensional representation of cyclohexane and its derivatives, characterized by a staggered arrangement of atoms that minimizes steric strain. This conformation allows for more stable interactions between substituents, making it crucial for understanding the spatial orientation of groups in cyclic compounds.
Recommended video:
Guided course
03:29
Understanding what a conformer is.
Cis and Trans Isomerism
Cis and trans isomerism refers to the different spatial arrangements of substituents around a double bond or a ring structure. In the context of cyclohexane derivatives, 'cis' indicates that substituents are on the same side of the ring, while 'trans' indicates they are on opposite sides, affecting the molecule's physical and chemical properties.
Recommended video:
Guided course
00:44Is the following cyclohexane cis or trans?
Planar Representation
The planar representation of a molecule simplifies its three-dimensional structure into a two-dimensional format, typically used for drawing and visualizing organic compounds. This representation is essential for understanding the connectivity and arrangement of atoms, especially when converting from a chair conformation to a flat depiction.
Recommended video:
Guided course
06:47Rules for Predicting Planarity
Related Practice
Textbook Question
Draw two chair conformations of the molecules below. Indicate which is most stable.
(a)
1
views
Textbook Question
Given the following chair conformations, draw each in its planar form as if you were viewing it from above.
(b)
4
views
Textbook Question
Draw two different chair conformations for each of the following molecules. Make sure that your drawings clearly show the cis–trans stereochemistry.
(c)
6
views
Textbook Question
Given the following chair conformations, draw each in its planar form as if you were viewing it from above.
(c)
1
views
Textbook Question
For each pair of conformations you drew in Assessment 3.41, indicate which is most stable.
1
views