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Ch.4 Introduction to Organic Compounds
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 1, Problem 76b

Determine whether each of the following is the cis or the trans stereoisomer:
(b)

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1
Identify the double bond in the molecule. A cis-trans isomerism occurs around a double bond where two different groups are attached to each carbon of the double bond.
Examine the groups attached to each carbon atom of the double bond. Determine the two substituents on each carbon.
For the cis isomer, the two identical or similar groups are on the same side of the double bond (both above or both below the plane of the double bond). For the trans isomer, the identical or similar groups are on opposite sides of the double bond (one above and one below the plane).
Compare the positions of the substituents on the double bond in the given image. Check if the identical or similar groups are on the same side (cis) or opposite sides (trans).
Based on the analysis, classify the given structure as either the cis or the trans isomer.

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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 physical and chemical properties. The two main types of stereoisomers are enantiomers and diastereomers, with cis and trans isomers being a specific type of diastereomer.
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Cis-Trans Isomerism

Cis-trans isomerism is a form of stereoisomerism where the isomers differ in the arrangement of substituents around a double bond or a ring structure. In cis isomers, similar groups are on the same side, while in trans isomers, they are on opposite sides. This distinction can significantly affect the physical properties of the compounds, such as boiling points and solubility.
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Identifying Isomers

To determine whether a compound is a cis or trans isomer, one must analyze the spatial arrangement of its substituents. This often involves visualizing the molecule's structure, particularly around double bonds or cyclic systems. Tools such as molecular models or drawings can help clarify the orientation of groups, allowing for accurate identification of the isomer type.
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Isomers Example 1