Textbook Question
Draw 1,2,3,4,5,6-hexachlorocyclohexane with
a. all the chloro groups in axial positions.
b. all the chloro groups in equatorial positions.
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Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure
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
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Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 48a,b,c
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 48a,b,cChapter 4, Problem 48a,b,c
Is each of the following a cis isomer or a trans isomer?
a, 
b. 
c. 
Verified step by step guidance1
Step 1: Understand the concept of cis and trans isomers. Cis isomers have substituents on the same side of a reference plane, while trans isomers have substituents on opposite sides of the reference plane.
Step 2: Analyze structure A. Identify the substituents (Br and NH2) and their positions relative to the cyclohexane ring. Determine if they are on the same side (cis) or opposite sides (trans).
Step 3: Analyze structure B. Identify the substituents (CH3 and OH) and their positions relative to the cyclohexane ring. Determine if they are on the same side (cis) or opposite sides (trans).
Step 4: Analyze structure C. Identify the substituents (OH and NH2) and their positions relative to the cyclohexane ring. Determine if they are on the same side (cis) or opposite sides (trans).
Step 5: Summarize the findings for each structure (A, B, and C) based on the spatial arrangement of the substituents and classify them as cis or trans isomers.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cis-Trans Isomerism
Cis-trans isomerism is a type of stereoisomerism where compounds have the same molecular formula but differ in the spatial arrangement of atoms. In cis isomers, similar groups are on the same side of a double bond or ring structure, while in trans isomers, they are on opposite sides. This difference can significantly affect the physical and chemical properties of the compounds.
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Is the following cyclohexane cis or trans?
Double Bonds and Restricted Rotation
Double bonds create a rigid structure that restricts rotation around the bond, allowing for the existence of cis and trans isomers. In alkenes, the presence of a double bond between carbon atoms prevents the free rotation that is possible in single bonds, leading to distinct geometric configurations. This rigidity is crucial for identifying and classifying isomers.
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Priority Rules in Isomer Identification
To determine whether a compound is a cis or trans isomer, priority rules based on the Cahn-Ingold-Prelog system are applied. These rules assign priority to substituents attached to the double-bonded carbons based on atomic number and connectivity. The arrangement of these high-priority groups relative to each other helps classify the isomer as cis or trans.
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Related Practice
Textbook Question
Draw the more stable chair conformer of cis-1-ethyl-2-methylcyclohexane.
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Textbook Question
The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane, considering rotation about the C1−C2 bond?
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Textbook Question
Using the data in Table 3.9, calculate the percentage of molecules of cyclohexanol that have the OH group in an equatorial position at 25 °C.
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Textbook Question
Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxialsubstituted conformer: trans-1,4-dimethylcyclohexane or cis-1-tert-butyl-3-methylcyclohexane?
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Textbook Question
Is each of the following a cis isomer or a trans isomer?
d.
e.
f.
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