Bayer's Strain theory - And Its Limitations - organic chemistry -2nd
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This document summarizes a student's presentation on Baeyer's strain theory and its limitations. The presentation covers: the introduction of Baeyer's theory that cycloalkanes strain is due to deviations from tetrahedral bond angles; the assumptions of planarity and increasing strain with ring size; limitations like inability to explain larger ring stabilities and observations contradicting predicted stabilities; and a case study showing Baeyer's predicted vs actual stability orders. The presentation is intended to help classmates understand Baeyer's theory of strain in cycloalkanes.
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The document discusses cyclohexane conformations and Baeyer's strain theory. It explains that the chair conformation is the most stable configuration for cyclohexane, while the boat conformation is less stable due to steric interactions. Baeyer's strain theory postulates that deviations from ideal tetrahedral bond angles impose strain on a molecule, with greater deviations resulting in greater instability. The theory explains the reactivity of small ring cycloalkanes like cyclopropane.
Baeyer's Strain theory.pptx
Cycloalkane stability is explained by Baeyer's Strain Theory, which states that deviations from the ideal tetrahedral bond angle of 109.5° impose strain. Cyclopropane has the most angle strain due to 60° bonds, making it highly unstable and prone to ring-opening. Cyclobutane has less strain from 90° bonds. Larger rings like cyclopentane and cyclohexane have less strain as their bond angles are closer to 109.5°. Baeyer assumed rings were flat, but they are actually puckered, allowing bonds to approach 109.5°. Rings larger than cyclopentane have little strain and are as stable as open-chain alkanes.
Coulsonand moffittsmodification
Coulson and Moffitt proposed that the carbon-carbon bonds in cyclopropane rings are bent based on quantum mechanical calculations. This idea of bent bonds is supported by electron density maps from X-ray studies. Molecular orbital theory explains that the overlap of orbital axes is maximized in cyclohexane, resulting in stronger carbon-carbon bonds, whereas in cyclopropane the orbital overlap is less, making the bonds weaker and allowing for ring-opening. Factors like bond angle strain from deviations from normal tetrahedral angles, torsional strain from non-staggered conformations, and steric strain from van der Waals repulsion between non-bonded atoms all contribute to the relative stability of different molecular conformations
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Cycloalkanes stability
This document discusses cycloalkanes, which are alkanes with some carbon atoms arranged in a ring. It covers the nomenclature, conformations, and relative stabilities of various cycloalkanes including cyclopropane, cyclobutane, cyclopentane, and cyclohexane. The most stable conformation of cyclohexane is the chair conformation, where all carbon-hydrogen bonds are staggered, minimizing angle and torsional strain. Substituted cyclohexanes can also adopt chair conformations, with substituents in either axial or equatorial positions.
Stabilities theory
Baeyer's strain theory proposed that deviations from the ideal tetrahedral bond angle of 109.5° cause instability in cycloalkane rings. It explained stability trends for the first few cycloalkanes but failed for larger rings. Sachse and Mohr proposed that larger rings avoid strain by being non-planar, with carbons in different planes allowing 109.5° angles. Coulson and Moffitt further explained stability using molecular orbital theory, that overlap of carbon orbitals is maximized at 109.5°, so deviation causes weaker bonds and more reactivity. This accurately describes stability trends, including cyclopropane being most reactive due to smallest angles limiting orbital overlap.
Sache mohr theory
Sachse-Mohr theory proposes that cyclic compounds like cyclohexane are not planar rings with strained carbon-carbon bonds, but rather exist in puckered, three-dimensional conformations that allow the carbon atoms to maintain their normal tetrahedral geometry and bond angles of 109.5 degrees without strain. Ernst Mohr later applied this theory to decalin, identifying its cis- and trans-isomers, supporting Sachse's hypothesis. The theory explains the observed stability of rings with six or more carbons and is now generally accepted.
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The document discusses cyclohexane conformations and Baeyer's strain theory. It explains that the chair conformation is the most stable configuration for cyclohexane, while the boat conformation is less stable due to steric interactions. Baeyer's strain theory postulates that deviations from ideal tetrahedral bond angles impose strain on a molecule, with greater deviations resulting in greater instability. The theory explains the reactivity of small ring cycloalkanes like cyclopropane.
Baeyer's Strain theory.pptx
Cycloalkane stability is explained by Baeyer's Strain Theory, which states that deviations from the ideal tetrahedral bond angle of 109.5° impose strain. Cyclopropane has the most angle strain due to 60° bonds, making it highly unstable and prone to ring-opening. Cyclobutane has less strain from 90° bonds. Larger rings like cyclopentane and cyclohexane have less strain as their bond angles are closer to 109.5°. Baeyer assumed rings were flat, but they are actually puckered, allowing bonds to approach 109.5°. Rings larger than cyclopentane have little strain and are as stable as open-chain alkanes.
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Coulson and Moffitt proposed that the carbon-carbon bonds in cyclopropane rings are bent based on quantum mechanical calculations. This idea of bent bonds is supported by electron density maps from X-ray studies. Molecular orbital theory explains that the overlap of orbital axes is maximized in cyclohexane, resulting in stronger carbon-carbon bonds, whereas in cyclopropane the orbital overlap is less, making the bonds weaker and allowing for ring-opening. Factors like bond angle strain from deviations from normal tetrahedral angles, torsional strain from non-staggered conformations, and steric strain from van der Waals repulsion between non-bonded atoms all contribute to the relative stability of different molecular conformations
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This document discusses cycloalkanes, which are alkanes with some carbon atoms arranged in a ring. It covers the nomenclature, conformations, and relative stabilities of various cycloalkanes including cyclopropane, cyclobutane, cyclopentane, and cyclohexane. The most stable conformation of cyclohexane is the chair conformation, where all carbon-hydrogen bonds are staggered, minimizing angle and torsional strain. Substituted cyclohexanes can also adopt chair conformations, with substituents in either axial or equatorial positions.
Stabilities theory
Baeyer's strain theory proposed that deviations from the ideal tetrahedral bond angle of 109.5° cause instability in cycloalkane rings. It explained stability trends for the first few cycloalkanes but failed for larger rings. Sachse and Mohr proposed that larger rings avoid strain by being non-planar, with carbons in different planes allowing 109.5° angles. Coulson and Moffitt further explained stability using molecular orbital theory, that overlap of carbon orbitals is maximized at 109.5°, so deviation causes weaker bonds and more reactivity. This accurately describes stability trends, including cyclopropane being most reactive due to smallest angles limiting orbital overlap.
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Sachse-Mohr theory proposes that cyclic compounds like cyclohexane are not planar rings with strained carbon-carbon bonds, but rather exist in puckered, three-dimensional conformations that allow the carbon atoms to maintain their normal tetrahedral geometry and bond angles of 109.5 degrees without strain. Ernst Mohr later applied this theory to decalin, identifying its cis- and trans-isomers, supporting Sachse's hypothesis. The theory explains the observed stability of rings with six or more carbons and is now generally accepted.
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The document summarizes Baeyer's strain theory, which proposed that cycloalkanes experience angle strain due to deviations from the normal tetrahedral bond angle of 109.5 degrees. Baeyer assumed cycloalkanes were planar, but this did not explain the stability of larger ring systems which are puckered rather than flat. The theory also incorrectly predicted cyclopentane would be more stable than cyclohexane. While Baeyer's theory provided insights, it had limitations and did not fully explain ring strain in different sized cycloalkane molecules.
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The document discusses cyclohexane conformations and Baeyer's strain theory. It explains that the chair conformation is the most stable configuration for cyclohexane, while the boat conformation is less stable due to steric interactions. Baeyer's strain theory postulates that deviations from ideal tetrahedral bond angles impose strain on a molecule, with greater deviations resulting in greater instability. The theory explains the reactivity of small ring cycloalkanes like cyclopropane.
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The document discusses cyclohexane conformations and Baeyer's strain theory. It explains that the chair conformation is the most stable configuration for cyclohexane, while the boat conformation is less stable due to steric interactions. Baeyer's strain theory postulates that deviations from ideal tetrahedral bond angles impose strain on a molecule, with greater deviations resulting in greater instability. The theory explains the reactivity of small ring cycloalkanes like cyclopropane.
PHYSICAL & CHEMICAL PROPERTIES.pptx
The document summarizes the physical, chemical, and combustion properties of cycloalkanes. It discusses how the properties change as the ring size increases. Smaller cycloalkanes like cyclopropane exhibit more reactivity due to ring strain from bond angles less than 109.5 degrees. Larger cycloalkanes like cyclohexane form stable chair and boat conformations without angle strain, making them less reactive. Baeyer's strain theory and Sachse-Mohr theory were proposed to explain the relative stabilities and reactivities of cycloalkanes based on ring strain.
Stereochemistry of cyclohexane.pptx
The document discusses stereochemistry of cyclohexane. It introduces cycloalkanes and Baeyer's strain theory, which proposed that angle strain increases with decreasing ring size. For cyclopropane and cyclobutane, the internal bond angles are much less than the ideal tetrahedral angle of 109.5 degrees, resulting in high angle strain. Sachse later suggested that cyclohexane exists as two stable chair conformations that are free of angle strain. Factors like angle strain, torsional strain, and nonbonded interactions like dipole-dipole interactions affect the stability of cyclic compound conformations. The chair and boat conformations of cyclohexane are discussed, along with equatorial and axial hydrogens and the
Stereochemistry of cyclohexane.pptx
Cyclohexane exists in stable chair and boat conformations. The chair conformation is more stable due to minimal angle and torsional strain. Substituents on cyclohexane can exist in axial or equatorial positions, with the equatorial position generally being more stable due to less 1,3-diaxial interactions. Disubstituted cyclohexanes can exist as cis or trans isomers, with the trans isomer being more stable for 1,2-disubstituted cyclohexanes due to less van der Waals strain.
Cycloalkanes
This document provides an overview of cycloalkanes. It begins with definitions and examples of cycloalkanes. It then discusses nomenclature and several methods for preparing cycloalkanes, including from dihalogen compounds, calcium salts of carboxylic acids, and esters of dicarboxylic acids. The document also summarizes theories for explaining the stability and properties of cycloalkanes, such as Baeyer's strain theory, the Coulson-Moffitt modification, and the Sachse-Mohr theory. Finally, it outlines some common chemical reactions of cycloalkanes, including substitution, addition (ring-opening), and oxidation reactions.
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Bayer's Strain theory - And Its Limitations - organic chemistry -2nd
- 2. DNCOP JAMGAON,SINNAR,NASIK SESSION : 2022-2023 COURSE : B PHARMA YEAR : 2nd SEMESTER : 4th SUBJECT : PHARMACEUTICAL ORGANIC CHEMISTRY - II TOPIC : BAEYER’S STRAIN THEORY AND ITS LIMITATIONS REPRESENTED BY:- Purushottam Mali Roll No - 60
- 3. ACKNOWLEDGEMENT I would like to express my special thanks of gratitude to our pharmaceutical organic chemistry-II professor respected “ Mrs. Bhagyashree Mam” ma'am who gave us the golden opportunity to do this wonderful presentation on topic ‘‘ Baeyer’s theory and its limitations”
- 4. CONTENT 1. INTRODUCTION OF BAEYER’S STRAIN THEORY 2. ASSUMPTION OF BAEYER’S STRAIN THEORY 3. LIMITATIONS OF BAEYER’S STRAIN THEORY 4. CASE STUDY ON BAEYER’S STRAIN THEORY 5. REFERENCES
- 5. INTRODUCTION OF BAEYER’S STRAIN THEORY 4. He assumes that all the cyclo-alkanes are fiat and coplanar that means they are two dimensional and present in one plane. Adolf von Baeyer, a German chemist and a Nobel prize winner from university of Munich, Germany in 1885 proposed a theory to explain the relative stability of the first few cycloalkane. The theory based on following facts: 1. Cyclo-alkanes are saturated compounds. So, all the carbons should have normal tetrahedral angle of 109.5° 2. Any deviation of bond angles from the normal tetrahedral value would, impose a condition of internal strain on the ring called angle strain. 3. More the value of angle strain less stable the compound is.
- 6. ASSUMPTIONS OF BAEYER’S STRAIN THEORY • All ring systems are planar. Deviation from normal tetrahedral angles results in to instable cycloalkanes. • The large ring systems involve negative strain hence do not exists. • The bond angles in cyclohexane and higher cycloalkanes (cycloheptane, cyclooctane, cyclononane, etc.) are not larger than 109.5° because the carbon rings of those compounds are not planar (flat).
- 7. LIMITATIONS OF BAEYER’S STRAIN THEORY • Baeyer was not able to explain the effect of angle strain in larger ring systems. • According to Baeyer Cyclopentane should be much stable than cyclohexane but practically it is reversed. • Larger ring systems are not possible according to Baeyer as they have negative strain but they exist and much stable. • Larger ring systems are not planar but wrinkled (puckered) to eliminate angle strain.
- 8. CASE STUDY ON BAEYER’S STRAIN THEORY According to Baeyer, the relative order of stability tor some common cycloalkanes is as under: Cyclopentane > Cyclohexane > Cyclobulane > Cyclopropane Actual observed order of stability for these cycloalkanes is as under: Cyclohexane > Cyclopentane > Cyclobutane > Cyclopropane
- 9. CASE STUDY ON BAEYER’S STRAIN THEORY According to Baeyer, the relative order of stability tor some common cycloalkanes is as under: Cyclopentane > Cyclohexane > Cyclobulane > Cyclopropane Actual observed order of stability for these cycloalkanes is as under: Cyclohexane Cyclopentane Cyclobutane Cyclopropane