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Chapter 22: Problem 40

Draw all the structural and geometrical (cis-trans) isomers of bromochloropropene.

Short Answer

Expert verified
There are four possible isomers of bromochloropropene: 1. Cis-1-bromo-2-chloropropene: \(\mathrm{(CHBr)}\) = \(\mathrm{CH} - \mathrm{CH}_2\mathrm{Cl}\) (cis-structure) 2. Trans-1-bromo-2-chloropropene: \(\mathrm{(CHBr)}\) = \(\mathrm{CH} - \mathrm{CH}_2\mathrm{Cl}\) (trans-structure) 3. 1-bromo-3-chloropropene: \(\mathrm{CHBr} = \mathrm{CH}_2 - \mathrm{CH}\mathrm{Cl}\) (one structural isomer with no geometrical isomers)

Step by step solution

01

Identify the Skeleton Structure of Propene

Propene has the molecular formula \(C_3H_6\), which has a double bond between the first and second carbon atoms, and single bonds between the second and third carbon atoms. The skeletal structure of the propene can be represented as \(\mathrm{CH}_2= \mathrm{CH} - \mathrm{CH}_3\). In bromochloropropene, one of the hydrogen atoms in propene will be substituted by a bromine atom, and another hydrogen atom by a chlorine atom.
02

Find Structural Isomers

Structural isomers are compounds with the same molecular formula, but different atom arrangements. To create structural isomers of bromochloropropene, we will replace one hydrogen atom with bromine and another one with chlorine. We need to consider the following options: 1. Replace hydrogen atoms on the first carbon atom. 2. Replace hydrogen atoms on the second carbon atom. 3. Replace one hydrogen atom on the first carbon atom and another one on the second carbon atom. Based on these considerations, we find that there are two possible structural isomers: 1. 1-bromo-2-chloropropene: \(\mathrm{CHBr} = \mathrm{CH} - \mathrm{CH}_2\mathrm{Cl}\) 2. 1-bromo-3-chloropropene: \(\mathrm{CHBr} = \mathrm{CH}_2 - \mathrm{CH}\mathrm{Cl}\)
03

Determine Geometrical Isomers for Given Structural Isomers

Geometrical isomers are compounds with the same connectivity but different spatial arrangements due to restricted rotation, usually around a double bond. They are also known as cis-trans isomers or E-Z isomers. For 1-bromo-2-chloropropene, the double bond between the first and second carbon atom restricts the rotation, and hence there can be two different spatial arrangements: 1. Cis-1-bromo-2-chloropropene (cis-structure): Bromine and chlorine atoms are on the same side of the double bond, with the structure looking like \(\mathrm{(CHBr)}\) = \(\mathrm{CH} - \mathrm{CH}_2\mathrm{Cl}\) 2. Trans-1-bromo-2-chloropropene (trans-structure): Bromine and chlorine atoms are on opposite sides of the double bond, with the structure looking like \(\mathrm{(CHBr)}\) = \(\mathrm{CH} - \mathrm{CH}_2\mathrm{Cl}\) For 1-bromo-3-chloropropene, the double bond is not between the carbon atoms with Bromine and Chlorine, so there are no geometrical isomers for this compound. In conclusion, there are four possible isomers for bromochloropropene: 1. Cis-1-bromo-2-chloropropene 2. Trans-1-bromo-2-chloropropene 3. 1-bromo-3-chloropropene

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Chemistry Education
Engaging in chemistry education involves far more than memorizing equations and chemical names; it includes developing a deep understanding of the principles that govern chemical behavior and reactions. One such principle is isomerism which is central to understanding molecular structure and function in organic chemistry. When educating students on complex topics like isomerism, it is crucial to employ strategies that simplify the concept without losing the essential details.

For instance, visual aids such as skeletal structures can help students better visualize molecules and their isomeric forms. Illustrating the three-dimensional arrangement of atoms within a molecule can clarify the differences between isomers. Additionally, providing analogies, hands-on activities, and real-life examples can make the content more relatable and easier to grasp. By using these educational tools, students can develop a comprehensive understanding of isomerism, which is fundamental in the study of all aspects of chemistry.
Organic Chemistry
At the heart of organic chemistry is the study of carbon-based compounds and their properties, reactions, and synthesis. It is a vast field with applications ranging from pharmaceuticals to materials science. A fundamental concept within organic chemistry is the formation of structural and geometrical isomers. This involves understanding how atoms in a molecule are connected and the implications of their spatial arrangement on the molecule's properties and reactivity.

In the case of bromochloropropene, recognizing the isomers requires an appreciation of the carbon skeleton of propene and how substituting different atoms can result in unique compounds with distinct properties, despite having the same molecular formula. This understanding is illustrative of the diverse possibilities within organic molecules and highlights the importance of a strong foundation in the principles of organic chemistry for the interpretation and prediction of chemical behavior.
Isomerism
Isomerism is a term that describes the phenomenon of compounds having the same molecular formula but differing in either their structure (structural isomers) or spatial arrangement (geometrical isomers). Mastery of this concept is essential for students of chemistry, as isomerism has profound implications on the physical and chemical properties of substances.

In structuring the explanation of isomerism for educational purposes, it's beneficial to start from the basic definitions and gradually build towards more complex examples, such as the cis-trans isomers of bromochloropropene. Emphasizing not only the theoretical aspects but also the real-world impacts, like how isomers can have drastically different smells, tastes, or biological activities, can enhance a student’s appreciation for the subject. Through detailed exploration and practice, students can solidify their understanding of isomerism and its critical role in the myriad forms and functions of organic compounds.

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