Geometrical isomers
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Geometrical isomers are compounds with the same molecular formula but different arrangements of functional groups on either side of a double or ring bond with restricted rotation. There are several types of geometrical isomers including cis-trans isomers, E-Z isomers, and syn-anti isomers. Cis isomers have functional groups on the same side of the carbon chain while trans have them on opposite sides. The configuration of double bond substituents is described as E or Z depending on the priority of the groups. Geometrical isomers can have different physical and chemical properties as well as biological activity.
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Geometrical isomerism
Geometrical isomers are compounds with the same molecular formula but different spatial arrangements of atoms or groups around a double bond. Geometrical isomerism arises from the inability of groups on opposite sides of a carbon-carbon double bond to rotate freely. Systems exhibiting geometrical isomerism include cis-trans isomers, where similar groups are on the same (cis) or opposite (trans) sides of the double bond, and E-Z isomers, where priority rules determine if higher priority groups are on the same (Z) or opposite (E) sides. Geometrical isomerism also occurs in compounds containing carbon-nitrogen or nitrogen-nitrogen double bonds.
Geometrical isomers
This document discusses geometrical isomers, which occur when rotation is restricted around a carbon-carbon double bond. Geometrical isomers can have different physical properties despite having the same molecular formula. The two types of geometrical isomers are cis-trans isomers and E-Z isomers. Cis-trans isomers have hydrogens on the same side (cis) or opposite sides (trans) of the double bond. E-Z isomers are assigned based on priority rules, with the Z isomer having higher priority groups on the same side and the E isomer having them on opposite sides. Examples are given of how geometrical isomers can impact drug action.
Unit II-Geometric isomerism and conformational isomer as PCI Syllabus of POC-III
It Includes Cis-Trans Isomer, E& Z Nomenclature, Syn and Anti isomer, Determination of geometrical isomer, Conformations of ethane, Butane, Cyclohexane, Stereospecific and stereoselective addition reactions.
Isomerism an introduction ,Geometrical Isomerism Syn Anti isomerism E-Z Isome...
Structural isomers have the same molecular formula but different structural formulas. There are several types of structural isomerism including chain, positional, and functional group isomerism. Stereoisomers have the same connectivity of atoms but different orientations in space. The main types of stereoisomerism are geometrical isomerism, optical isomerism, and conformational isomerism. Geometrical isomerism occurs due to restricted bond rotation and results in cis-trans, syn-anti, and E-Z isomers.
Unit i.Optical Isomerism as per PCI syllabus of POC-III
Unit I optical isomerism which is included in PCI syllabus of Sem IV of POC-III subject
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Unit II Geometrical isomerism
The document provides information about geometrical isomerism including definitions, examples, and methods of determination. It defines geometrical isomerism as arising from restricted rotation around a double bond that leads to different spatial arrangements of atoms. Common types of geometrical isomers include cis-trans, E-Z, and syn-anti. Methods for determining configurations include cyclization reactions, conversion to compounds of known configuration, differences in physical properties, and use of stereoselective or stereospecific reactions.
Optical isomerism
This document discusses isomerism and stereochemistry. It defines isomers as compounds with the same molecular formula but different structures or arrangements. Isomerism includes structural isomers like chain, positional, and functional isomers as well as stereoisomers. Stereoisomers have the same connectivity but different spatial arrangements and include enantiomers, which are non-superimposable mirror images, and diastereomers. Chiral molecules lack symmetry elements like planes and centers of symmetry and cannot be superimposed on their mirror images, while achiral molecules can.
Geometrical Isomerism
This document discusses different types of isomers, including structural isomers, stereoisomers, and geometric isomers. It provides examples of cis-trans isomers, which are a type of geometric isomer that can exhibit different optical properties depending on their spatial arrangement. Geometric isomers containing double bonds can exist as cis or trans configurations. Cyclohexane derivatives can also exhibit cis-trans isomerism, with trans configurations sometimes being optically active whereas cis configurations are optically inactive. In summary, the document covers the key types and examples of isomers, focusing on geometric isomers and cis-trans isomerism.
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Geometrical isomerism
Geometrical isomers are compounds with the same molecular formula but different spatial arrangements of atoms or groups around a double bond. Geometrical isomerism arises from the inability of groups on opposite sides of a carbon-carbon double bond to rotate freely. Systems exhibiting geometrical isomerism include cis-trans isomers, where similar groups are on the same (cis) or opposite (trans) sides of the double bond, and E-Z isomers, where priority rules determine if higher priority groups are on the same (Z) or opposite (E) sides. Geometrical isomerism also occurs in compounds containing carbon-nitrogen or nitrogen-nitrogen double bonds.
Geometrical isomers
This document discusses geometrical isomers, which occur when rotation is restricted around a carbon-carbon double bond. Geometrical isomers can have different physical properties despite having the same molecular formula. The two types of geometrical isomers are cis-trans isomers and E-Z isomers. Cis-trans isomers have hydrogens on the same side (cis) or opposite sides (trans) of the double bond. E-Z isomers are assigned based on priority rules, with the Z isomer having higher priority groups on the same side and the E isomer having them on opposite sides. Examples are given of how geometrical isomers can impact drug action.
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Structural isomers have the same molecular formula but different structural formulas. There are several types of structural isomerism including chain, positional, and functional group isomerism. Stereoisomers have the same connectivity of atoms but different orientations in space. The main types of stereoisomerism are geometrical isomerism, optical isomerism, and conformational isomerism. Geometrical isomerism occurs due to restricted bond rotation and results in cis-trans, syn-anti, and E-Z isomers.
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The document provides information about geometrical isomerism including definitions, examples, and methods of determination. It defines geometrical isomerism as arising from restricted rotation around a double bond that leads to different spatial arrangements of atoms. Common types of geometrical isomers include cis-trans, E-Z, and syn-anti. Methods for determining configurations include cyclization reactions, conversion to compounds of known configuration, differences in physical properties, and use of stereoselective or stereospecific reactions.
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This document discusses isomerism and stereochemistry. It defines isomers as compounds with the same molecular formula but different structures or arrangements. Isomerism includes structural isomers like chain, positional, and functional isomers as well as stereoisomers. Stereoisomers have the same connectivity but different spatial arrangements and include enantiomers, which are non-superimposable mirror images, and diastereomers. Chiral molecules lack symmetry elements like planes and centers of symmetry and cannot be superimposed on their mirror images, while achiral molecules can.
Geometrical Isomerism
This document discusses different types of isomers, including structural isomers, stereoisomers, and geometric isomers. It provides examples of cis-trans isomers, which are a type of geometric isomer that can exhibit different optical properties depending on their spatial arrangement. Geometric isomers containing double bonds can exist as cis or trans configurations. Cyclohexane derivatives can also exhibit cis-trans isomerism, with trans configurations sometimes being optically active whereas cis configurations are optically inactive. In summary, the document covers the key types and examples of isomers, focusing on geometric isomers and cis-trans isomerism.
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Geometrical isomerism
Geometrical isomerism refers to structural isomers that differ in the orientation of functional groups around a double bond or ring structure. There are three main systems used to name geometrical isomers: cis-trans, E-Z, and syn-anti. Cis-trans nomenclature refers to whether identical groups are on the same side (cis) or opposite sides (trans) of a double bond. E-Z nomenclature is used when all four substituents are different. Syn-anti refers to whether substituents are on the same side (syn) or opposite sides (anti) of a carbon-nitrogen double bond. Various methods can be used to determine the configuration of geometrical is
Geometric isomerism
For B.Pharm 4th sem student
The isomerism which occurs due to difference of the positions of the substituents about a double bond or a ring due to restricted rotation is called geometric isomerism.
They do not rotate the plane of polarised light (unless they also happen to be chiral), and do not have identical properties.
Oxazole
Oxazole is a five-membered heterocyclic aromatic compound containing one oxygen atom and one nitrogen atom. It has a planar cyclic structure and follows Hückel's rule for aromaticity. Oxazole can be synthesized through the Robinson–Gabriel synthesis involving an intramolecular cyclization of a 2-acylamino-ketone. It can also be synthesized through the reaction of acid amides with α-haloketones or α-hydroxyketones. The Van Leusen reaction involving a ketone and TosMIC leads to the formation of an oxazole through a 5-endo-dig cyclization. Oxazole undergoes electrophilic aromatic substitution at C5 with activating
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The document discusses the representation and nomenclature of optical isomers. It defines:
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- The D/L and R/S systems for assigning configuration to chiral centers. The D/L system uses hydroxy acid/amino acid and sugar conventions while the R/S system uses Cahn-Ingold-Prelog priority rules.
- Sequence rules for assigning priority to groups around a chiral center in the R/S system.
- Methods for determining R/S configuration including orientation of the lowest priority group and interchanging groups in Fischer projections.
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Benzilic acid rearrangement. The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid.
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Stereochemistry
Stereochemistry is the branch of chemistry concerned with the three-dimensional arrangement of atoms in molecules and how this affects chemical reactions. Stereoisomerism occurs when molecules have the same chemical structure but different spatial arrangements of atoms. Optical isomers, also known as enantiomers, are stereoisomers that are non-superimposable mirror images and differ only in their ability to rotate plane-polarized light. For a molecule to exhibit optical isomerism, it must contain an asymmetric carbon atom and lack a plane of symmetry.
Resolution of racemic mixture
1. Enantiomers are chiral isomers that are non-superimposable mirror images of each other. A racemic mixture contains equal amounts of both enantiomers.
2. Resolution is the separation of a racemic mixture into its individual enantiomers. This can be done using mechanical, biochemical, chemical, or enzymatic methods.
3. Chemical resolution involves converting the racemic mixture into diastereomers using an optically pure resolving agent. The diastereomers have different properties and can be separated.
Racemisation and method of resolution
Racemisation is the process where a pure enantiomer is converted into a 50/50 mixture of both enantiomers, called a racemate. This can occur through various chemical reactions or physical changes that allow for inversion or interchange of chiral centres. Resolution is the separation of the enantiomers in a racemate. Several methods can be used to induce and monitor racemisation, such as changes in pH, temperature, catalysts, or conformational changes. Resolution techniques include forming diastereomeric salts, molecular complexes, or exploiting kinetic or thermodynamic differences in reactions.
Isomers and isomerism
Isomers are compounds that have the same molecular formula but different structural formulas or different arrangements of atoms in space. The two main types of isomerism are structural isomerism and stereoisomerism. Structural isomers have the same molecular formula but differ in their bonding connectivity or types of functional groups. Stereoisomers have the same structural formula but different spatial arrangements of atoms. Examples of stereoisomers are cis-trans isomers and enantiomers.
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Oxazole
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The document discusses the representation and nomenclature of optical isomers. It defines:
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- The D/L and R/S systems for assigning configuration to chiral centers. The D/L system uses hydroxy acid/amino acid and sugar conventions while the R/S system uses Cahn-Ingold-Prelog priority rules.
- Sequence rules for assigning priority to groups around a chiral center in the R/S system.
- Methods for determining R/S configuration including orientation of the lowest priority group and interchanging groups in Fischer projections.
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Benzilic acid rearrangement. The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid.
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Stereochemistry
Stereochemistry is the branch of chemistry concerned with the three-dimensional arrangement of atoms in molecules and how this affects chemical reactions. Stereoisomerism occurs when molecules have the same chemical structure but different spatial arrangements of atoms. Optical isomers, also known as enantiomers, are stereoisomers that are non-superimposable mirror images and differ only in their ability to rotate plane-polarized light. For a molecule to exhibit optical isomerism, it must contain an asymmetric carbon atom and lack a plane of symmetry.
Resolution of racemic mixture
1. Enantiomers are chiral isomers that are non-superimposable mirror images of each other. A racemic mixture contains equal amounts of both enantiomers.
2. Resolution is the separation of a racemic mixture into its individual enantiomers. This can be done using mechanical, biochemical, chemical, or enzymatic methods.
3. Chemical resolution involves converting the racemic mixture into diastereomers using an optically pure resolving agent. The diastereomers have different properties and can be separated.
Racemisation and method of resolution
Racemisation is the process where a pure enantiomer is converted into a 50/50 mixture of both enantiomers, called a racemate. This can occur through various chemical reactions or physical changes that allow for inversion or interchange of chiral centres. Resolution is the separation of the enantiomers in a racemate. Several methods can be used to induce and monitor racemisation, such as changes in pH, temperature, catalysts, or conformational changes. Resolution techniques include forming diastereomeric salts, molecular complexes, or exploiting kinetic or thermodynamic differences in reactions.
Isomers and isomerism
Isomers are compounds that have the same molecular formula but different structural formulas or different arrangements of atoms in space. The two main types of isomerism are structural isomerism and stereoisomerism. Structural isomers have the same molecular formula but differ in their bonding connectivity or types of functional groups. Stereoisomers have the same structural formula but different spatial arrangements of atoms. Examples of stereoisomers are cis-trans isomers and enantiomers.
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This document defines heterocyclic compounds and outlines their nomenclature, classification, properties, synthesis, and medicinal importance. Heterocyclic compounds contain at least one heteroatom such as nitrogen, oxygen, or sulfur within their cyclic structure. The document discusses IUPAC and common naming systems and classifies heterocycles by nature and number of heteroatoms, degree of saturation, and ring size. Examples of important heterocyclic drug classes are provided, including imidazoles, benzimidazoles, pyridines, quinolines, barbiturates, and others. The key objectives, properties, reactions, and medical relevance of heterocyclic compounds are summarized.
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Unit iii heterocyclic compounds as per PCI Syllabus of POC-III
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Isomers are compounds that have the same molecular formula but different structural or spatial arrangements. There are several types of isomers including structural isomers, stereoisomers, and optical isomers. Structural isomers have the same atoms bonded differently. Stereoisomers have the same bonding but different 3D orientations. Optical isomers cannot be superimposed and rotate plane-polarized light in opposite directions. Isomers are important in drug development and biological processes because evolution favors specific isomer forms for functions. The structures and positions of groups in isomers strongly influence chemistry and pharmaceutical manufacturing.
Food chemistry
This document discusses stereochemistry in food, specifically enantiomers. It begins by defining chiral carbon atoms and how they give rise to two distinct spatial arrangements called enantiomers. While enantiomers are mirror images with identical physical and chemical properties, they differ in how they rotate polarized light. The document then covers three naming conventions - D,L notation used for sugars and amino acids; R,S system (CIP system); and differences in properties between enantiomeric forms like differing tastes, smells, and toxicity. Enantiomers found in nature are often pure forms produced through stereospecific biosynthesis, while synthetic equivalents are often racemic mixtures for easier production.
Stereochemistry
The document discusses various topics in stereochemistry including:
1. Stereochemistry deals with the three dimensional structure of molecules and how it affects properties.
2. Isomers can be classified as structural, positional, functional, ring-chain, metamers, and tautomeric depending on their structure.
3. Chiral molecules have "handedness" and lack a plane of symmetry, allowing the existence of enantiomers which are non-superimposable mirror images. Systems like R/S, D/L, and E/Z are used to describe chiral molecule stereochemistry.
STEREOCHEMISTRY.pptx
e-content of Stereochemistry for Pharmacy and Chemistry students.
contents includes Isomerism, Chirality, Stereoisomers, Enantiomer, Diastereomer, Cis And Trans Configuration ,L And D Configuration ,R And S Configuration and Importance of the chirality in drugs ,Intravenous anaesthetics , etc.
4.stereochem1
1. The document discussed different types of isomers including constitutional isomers, which have the same molecular formula but different connectivity, and stereoisomers, which have the same connectivity but different spatial arrangements.
2. Conformational isomers result from rotation about single bonds, while configurational isomers include cis-trans isomers of alkenes and cyclic alkanes.
3. Isomerism, including constitutional, stereoisomers, conformational isomers, and configurational isomers, arises from different
STEREOCHEMISTRY.pptx
This document provides an overview of stereochemistry concepts including:
- Stereoisomers such as configurational, conformational, geometrical, optical isomers and relationships between them.
- Rules for assigning R/S and E/Z descriptors using the Cahn-Ingold-Prelog priority system to name stereoisomers.
- Cis-trans nomenclature for geometrical isomers and its limitations.
- Fischer's D-L notation for distinguishing carbohydrates and amino acid enantiomers and determining configurations.
- Meso compounds which are achiral despite having multiple stereocenters due to an internal plane of symmetry.
(24) session 24 stereochemistry
1) The document discusses stereochemistry and isomers. It defines key terms like stereoisomers, enantiomers, chiral centers, and optical activity.
2) Enantiomers are nonsuperimposable mirror images that are chiral and optically active, rotating plane-polarized light in opposite directions.
3) The R/S system is used to assign configurations to chiral molecules and stereocenters according to Cahn-Ingold-Prelog priorities.
Stereochemistry
Stereochemistry is the systematic presentation of a specific field of science and technology that traditionally requires a short preliminary excursion into history. Stereochemistry is the ‘chemistry of space ‘, that is stereochemistry deals with the spatial arrangements of atoms and groups in a molecule.
Stereochemistry can trace its roots to the year 1842 when the French chemist Louis Pasteur made an observation that the salts of tartaric acid collected from a wine production vessel have the ability to rotate plane-polarized light, whereas the same salts from different sources did not have this ability. This phenomenon is explained by optical isomerism.
Basic aspects of Stereochemistry
This document provides an overview of stereochemistry. It begins by defining constitutional and stereoisomers. Stereoisomers have the same connectivity but different arrangements in space, and include enantiomers and diastereomers. The document then discusses chiral centers and molecules, and how the presence of a chiral center leads to chirality. It also covers topics such as optical activity, properties of enantiomers and diastereomers, meso compounds, geometric isomers, and resolving racemic mixtures. Resolution methods discussed include conversion to diastereomers and differential absorption chromatography.
Stereochemistry part 3 Geometrical isomerism
CIS/ TRANS, E/Z nomenclature,
The term cis - is used when two similar atoms or groups are present on same sides across the double bond and the term trans - is used when two similar atoms or groups are
present on opposite sides across the double bond.
Ch 5 Stereochemistry 2014.ppt
1. The document covers stereochemistry and isomers, including constitutional and cis-trans isomers.
2. It discusses chiral and achiral molecules, and defines enantiomers as nonsuperimposable mirror images that have the same physical and chemical properties.
3. Key concepts covered include asymmetric centers, optical activity, and using priority rules to determine R and S configurations around chiral centers.
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Geometrical isomers
- 1. Geometrical isomers Presented by- Ranadeep Borgohain M.Pharm 2nd Semester Department of Pharmacy Tripura University 1
- 2. CONTENT • What is isomer? • Classification of isomer • What is geometrical isomer? • Characteristics of geometrical isomer • Cis-tran isomer • E-Z isomer • Rules for finding E-Z isomer • Syn-anti isomers • Use of geometrical isomer • Reference 2
- 3. What is isomer? • Compounds that have the same molecular formula. 1 2 3 4 H H H H H H H H H H butane CH3 CH3 CH3 isobutane 3
- 4. CONSTITUTIONAL ISOMERS STERIOISOMERS CONFORMATIONAL ISOMERS CONFIGURATIO NAL ISOMERS ROTATION ABOUT SINGLE BODIES AMINE INVERSION GEOMETRIC AL ISOMERS ISOMERS CONTAINING CHIRAL CENTRES CIS-TRANS ISOMERS E-Z ISOMERS SYN ANTI ISOMERS 4
- 6. What is geometrical isomers? • Compounds with different arrangements of groups on either side of a bond with restricted rotation, such as a double bond or a single bond in a ring 6
- 7. Characteristics of geometrical isomer • Different physical properties - Different density - Polarity - solubility - melting point - boiling point • Different arrangement 7
- 8. CIS-TRANS ISOMERS • Cis isomers are the isomers where functional group are on the same side of the carbon chain. CH3 CH3 H H cis-but-2-ene 8
- 9. • Trans isomers are the isomers where the functional groups are on opposing sides of the carbon chain. CH3 CH3H H trans-but-2-ene 9
- 10. E-Z ISOMERS • It is an extension of Cis–trans isomer notation that can be used to describe double bonds having two, three or four substituent. • If the two groups of higher priority are on opposite sides of the double bond, the bond is assigned the configuration E . E-But-2-ene 10
- 11. • If the two groups of higher priority are on the same side of the double bond, the bond is assigned the configuration Z . (Z)-But-2-ene 11
- 12. RULES FOR FINDING E-Z ISOMERS • Rule 1: high atomic number high priority CH3 Br Cl H The z isomer Cl Br CH3 H The E isomer 12
- 13. • Rule 2: If an atom is doubly bonded to another atom, the priority system treats it as if it were singly bonded to two of those atoms. If an atom is triply bonded to another atom, the priority system treats it as if it were singly bonded to three of those atoms. 13
- 14. • Rule3: In the case of isotopes (atoms with the same atomic number, but different mass numbers), the mass number is used to determine the relative priorities CH3 CH3 CH2 H D The Z isomer CH2 CH3 CH3 H D The E isomer 14
- 15. SYN- ANTI ISOMERS • This type used for stereoisomeric oxime. Anti isomer Where H and OH is trans syn isomer Where H and OH is ciz N OH H NOH H 15
- 16. USE OF GEOMETRICAL ISOMERS H H OH OH H H OH OH trans-DEC cis-DES (Estrogenic) (non estrogenic) 16
- 17. H N NCH3 Triprolidine (E) Trans isomer, i.e., E, is 1000-times more histaminic than cis, Z 17
- 18. Me MeMe OH Vitamin A has all E double bonds, any Z would make it inactive! 18
- 19. REFERENCE • https://www.slideshare.net/dragnerkar • https://www.slideshare.net/sofiamubashir • https://m.youtube.com/watch?v=hyWgF6Dnit Y • https://www.chemguide.co.uk/basicorg/isom erism/geometric.html 19
- 20. 20