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Ch.4 Introduction to Organic Compounds
Chapter 1, Problem 4.33b

Determine if each of the following cycloalkanes or alkenes can exist as cis–trans stereoisomers. For those that can, draw the two isomers. Label each of the isomers you drew as the cis stereoisomer or the trans stereoisomer.


(b) CH₃CH₂CH₂CH₂CH=CH₂

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1
Identify the type of compound: The given compound is an alkene, as indicated by the presence of a carbon-carbon double bond (C=C).
Determine the possibility of cis-trans isomerism: For cis-trans isomerism to occur, each carbon atom in the double bond must have two different groups attached to it.
Analyze the structure: The compound is CH₃CH₂CH₂CH₂CH=CH₂. The double bond is between the fifth and sixth carbon atoms.
Check the substituents on the double-bonded carbons: The fifth carbon (CH) is attached to a propyl group (CH₂CH₂CH₃) and a hydrogen atom, while the sixth carbon (CH₂) is attached to two hydrogen atoms.
Conclude the possibility of isomerism: Since the sixth carbon has two identical groups (hydrogens), the compound cannot exhibit cis-trans isomerism.

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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, also known as geometric isomerism, occurs in compounds with restricted rotation around a double bond or within a ring structure. In alkenes, the 'cis' configuration has substituents on the same side of the double bond, while the 'trans' configuration has them on opposite sides. This spatial arrangement can significantly affect the physical and chemical properties of the compounds.
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Cycloalkanes and Alkenes

Cycloalkanes are saturated hydrocarbons with carbon atoms arranged in a ring, while alkenes are unsaturated hydrocarbons containing at least one carbon-carbon double bond. The presence of a double bond in alkenes allows for the possibility of cis-trans isomerism, depending on the substituents attached to the double-bonded carbons. Understanding the structure of these compounds is essential for identifying isomerism.
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Drawing Isomers

Drawing isomers involves representing the different spatial arrangements of atoms in a molecule. For cis-trans isomers, it is important to accurately depict the orientation of substituents around the double bond. Labeling each isomer as 'cis' or 'trans' helps clarify their differences, which is crucial for understanding their reactivity and properties in chemical reactions.
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Related Practice
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Textbook Question

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