Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

13. Alkenes, Alkynes, and Aromatic Compounds

Isomers

GOB Chemistry

13. Alkenes, Alkynes, and Aromatic Compounds

Isomers

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Problem 82

Textbook Question

Why do you suppose small-ring cycloalkenes like cyclohexene do not exist as cis–trans isomers, whereas large ring cycloalkenes like cyclodecene do show isomerism?

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Understand the concept of cis-trans isomerism: Cis-trans isomerism occurs in alkenes when there is restricted rotation around the double bond and two different groups are attached to each carbon of the double bond. The spatial arrangement of these groups determines whether the isomer is 'cis' (same side) or 'trans' (opposite sides).

Examine the structure of small-ring cycloalkenes like cyclohexene: In small-ring cycloalkenes, the ring size imposes significant geometric constraints. The double bond in cyclohexene is part of a six-membered ring, and the ring's rigidity forces the substituents on the double-bonded carbons to be on the same side of the ring. This makes the 'trans' configuration impossible due to severe ring strain.

Compare with large-ring cycloalkenes like cyclodecene: In larger rings, such as cyclodecene (10-membered ring), the ring is more flexible and can accommodate both 'cis' and 'trans' configurations without introducing excessive strain. This flexibility allows for the existence of cis-trans isomerism in large-ring cycloalkenes.

Relate to ring strain: Small rings experience significant ring strain due to bond angle deviations from the ideal tetrahedral angle (109.5°). Introducing a 'trans' configuration in a small ring would further increase this strain, making it energetically unfavorable. Larger rings, however, have bond angles closer to the ideal and can adopt conformations that reduce strain, allowing for both isomers.

Conclude the reasoning: Small-ring cycloalkenes like cyclohexene cannot exhibit cis-trans isomerism because the ring's rigidity and strain prevent the formation of a stable 'trans' isomer. In contrast, large-ring cycloalkenes like cyclodecene are flexible enough to adopt both 'cis' and 'trans' configurations, enabling 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 bond, typically a double bond or a ring structure. In this type of isomerism, the spatial arrangement of substituents differs, leading to distinct physical and chemical properties. For small-ring cycloalkenes, such as cyclohexene, the ring's strain and flexibility prevent the formation of stable cis and trans configurations.

Ring Strain

Ring strain refers to the increased energy and instability in cyclic compounds due to bond angles deviating from the ideal tetrahedral angle of 109.5 degrees. In small rings like cyclohexene, the angles are significantly distorted, leading to high strain and making it energetically unfavorable for the molecule to adopt different isomeric forms. Larger rings, such as cyclodecene, have more flexibility and can accommodate different spatial arrangements without significant strain.

Conformational Flexibility

Conformational flexibility is the ability of a molecule to adopt different shapes or conformations due to rotation around single bonds or the ability to bend in larger rings. In larger cycloalkenes, such as cyclodecene, the increased number of atoms allows for various conformations that can lead to stable cis and trans isomers. This flexibility contrasts with smaller rings, where the limited conformational options restrict isomer formation.