25:["$","title",null,{"children":"Module 03 Geometric Isomerism and conformational isomerism Restricted vs free rotation | OrganChem | Observable"}] 49:T893,**Geometric Isomerism in Alkenes** The carbon atom of the carbon-carbon double bond is $sp^2$ hybridized. The $\ce{C-C}$ double bond consists of a sigma bond and a pi-bond. The sigma bond is formed via the overlap of $sp^2$ hybrid orbitals, while the pi-bond is formed by the overlap of $p$-orbitals. The presence of pi-bond locks the molecule in one position. The two carbon atoms of the $\ce{C=C}$ bond and the four atoms that are attached to them lie in one plane and their position in space is fixed. Therefore, rotation around the $\ce{C=C}$ bond is not possible because rotation would break the pi-bond. **This restriction of rotation about the carbon double bond is responsible for the geometric isomerism in alkenes.** For example, 2-butene exists in two spatial arrangements i.e., cis-2-butene and trans-2-butene. ![](${await FileAttachment('geometric1.png').url()}) These two compounds are referred to as geometric isomers. These geometric isomers are stereoisomers because they have the same structural formula but different arrangements of atoms in space. They are distinguished from each other by the term cis or trans. **The cis isomer is one in which the two similar groups are on the same side of the double bond. While the trans isomer has two similar groups on the opposite sides of the double bond.** **Geometric isomerism is only possible when each double bonded carbon atom is attached to two different atoms or groups.** In propene, geometric isomerism is not possible because one carbon on the double bonded carbon has **two identical groups** (H atoms) attached to it. However, a geometric isomer is possible because each double bonded carbon is attached to two **different groups** ($\ce{CH3CH2}$ and H) attached to it. ![](${await FileAttachment('geometric2.png').url()}) The trans isomers are more stable than the corresponding cis isomer because in cis isomer the bulky groups are on the same side of the double bond. The steric repulsion of the groups makes the cis isomer least stable. ![](${await FileAttachment('geometric3.png').url()}) These isomers also differ in physical properties such as melting point, dipole moment and acidities. 4a:T481,**Geometric Isomerism in Cyclic Compounds** Geometric isomerism is also possible in cycloalkanes. There can be no rotation about carbon-carbon single bonds forming a ring because rotation would break the bonds and break the ring. For example, 1,2-dimethylcyclopropane exist in isomeric forms. ![](${await FileAttachment('cyclic1.png').url()}) **A cyclic compound must have at least two other groups besides hydrogens on the ring and these must be on different ring carbons.** ![](${await FileAttachment('cyclic2.png').url()}) ![](${await FileAttachment('cyclic3.png').url()}) Geometric isomerism is also possible in other compounds such as aldoximes, ketoximes etc. ![](${await FileAttachment('cyclic4.png').url()}) *Additional reading* Geometric Isomerism See VIDEO [Cis-trans and E-Z naming scheme for alkenes](https://youtu.be/oYoQpDtBLac) 4b:T4ec,**Torsional strain** Torsional strain or eclipsing strain is the increase in the potential energy of a molecule due to repulsion between electrons in bonds that do not share an atom. Among the two conformations of ethane, the torsional strain is maximum in the eclipsed conformation (dihedral angle = 0) and minimum in the staggered conformation (dihedral angle = 60). **Steric strain** Steric strain is the increase in the potential energy of a molecule due to repulsion between electrons in atoms that are not directly bonded to each other. In conformations where bulky atoms on adjacent carbon atoms are close to each other, there is a large amount of steric strain. ![](${await FileAttachment('conform6.png').url()}) Structures 1 and 2 above are both staggered conformations but the structure has greater steric strain because the two bulky bromine atoms are closer. *Additional reading* Conformational analysis of alkanes See VIDEO [Conformational analysis of ethane](https://youtu.be/vOq6cwT-l2U) [Conformational analysis of propane](https://youtu.be/lIJ45KYQOLM) [Conformational analysis of butane](https://youtu.be/dTst62XXJ8g) 4c:T765,**Conformations of cycloalkanes** The conformations of cycloalkanes are determined by torsional strain, steric strain and angle strain. For an $sp^3$ hybridized carbon atom, the ideal bond angle is 109.5 $^\circ$ (tetrahedral bond angle). Angle strain is the extra energy that a compound has because of non-ideal bond angles (i.e., angles above or below 109.5 $^\circ$) ![](${await FileAttachment('conform7.png').url()}) *Additional reading* Stability of cycloalkanes – Ring strain Conformations of cycloalkanes See VIDEOS [Stability of cycloalkanes](https://youtu.be/DXc4pa9lIaA) [Conformations of cycloalkanes](https://www.youtube.com/watch?v=t-QtRpYbKBg&t=178s) [Conformations of cyclohexane-1](https://youtu.be/YUEkOBvJSNg) [Conformations of cyclohexane-2](https://youtu.be/p9NzhA3E-70) [Drawing chair conformations](https://youtu.be/AtK0QQYHKCk) [Conformations of monosubstituted cyclohexane](https://youtu.be/kNQnnshdNuo) [Conformations of disubstituted cyclohexane](https://youtu.be/TI27-ZN2Glg) *Additional reading* Geometric isomerism in disubstituted cyclohexane 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29:{"id":"a2c3ea3d45e5d2bc","slug":null,"title":"Module 03 Geometric Isomerism and conformational isomerism Restricted vs free rotation","thumbnail":"6fc9e3c869cb88d8369ae3f6e8a7372c008f38cc28d7bbbb95fa71f9cb92f48a","access_level":"public","create_time":"$D2023-05-11T19:56:22.718Z","update_time":"$D2023-05-15T21:27:19.833Z","view_time":null,"first_public_time":"$D2023-05-11T19:56:22.718Z","has_unpublished_edits":null,"fork":{"id":"8256f1c92eeba0cb","slug":null,"title":"Module 02 Optical Isomerism - Chirality and its consequences","owner":{"id":"413d80f47db57e44","login":"organchem","name":"OrganChem"}},"stars":0,"starred":false,"owner":{"type":"team","id":"413d80f47db57e44","login":"organchem","name":"OrganChem","avatar_url":"https://avatars-next.observableusercontent.com/a6bcbd733d16171eb1b0884f56a848d39052524bbdeac3f0f495d866031181f0","tier":"starter_2024","bio":"Organic Chemistry education 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Wang","avatar_url":"https://avatars-next.observableusercontent.com/65bf9b9dfeacc117351e386728523834c1c0beb4bf838d82678844a0aea65ecb","tier":null,"role":"editor"}],"comments":[],"custom_thumbnail":false,"trashed":false,"lapsed":null,"subscribed":null,"forks":1,"collection":{"id":"1199aa0ef269999f","slug":"organchem","title":"Stereochemistry","owner":{"id":"413d80f47db57e44","login":"organchem","name":"OrganChem"}},"type":"notebook","body":{"titling":"auto","title":"Module 03 Geometric Isomerism and conformational isomerism Restricted vs free rotation","cells":[{"id":531,"value":"# Module 03 Geometric Isomerism and conformational isomerism Restricted vs free rotation","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":12,"value":"front","pinned":false,"hidden":false,"mode":"ojs","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"$undefined","database":"$undefined"},{"id":552,"value":"## 3.1 Geometric (cis - trans) isomerism","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":554,"value":"The different geometrical arrangements of the groups about the doubly bonded carbon atom or about a ring is known as Geometrical isomerism. When the similar groups lie on the same side it is called the Cis isomer (Latin, cis. = on same side). When similar groups are on the opposite sides, it is called the trans isomer (Latin, trans = across). Geometric isomers possess the same structural formula and differ only in respect of the arrangement of atoms or groups about the double bond or a ring.","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":556,"value":"$49","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":558,"value":"**Assigning Configurations to Alkenes** \n\nThe configuration of geometric isomers can be designated as cis or trans but for some alkenes, this cis-trans method does not work. Hence, the configuration of all the geometric isomers can be specified by the **E-Z system**.\n\n**E-Z System**\n\nThis system can be used to specify the configuration of any carbon-carbon double bond unambiguously by using the system devised by **R.S. Cahn, C.K.Ingold and V. Prelog. (CIP rules – Refer Module 2)** \n**Z** derived from German, zusammen = together, whereas, \n**E** from German, entgegen = opposite \n•E-alkenes have the groups of highest priority on the opposite sides \n•Z-alkenes have the groups of highest priority on the same sides.\n \n![](${await FileAttachment('EZ1.png').url()})","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":560,"value":"**Check your understanding 1**\n\nFor the following molecules write proper E/Z labels. \n\n![](${await FileAttachment('check1.png').url()})","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":562,"value":"$4a","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":564,"value":"## 3.2 Conformational isomerism","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":566,"value":"Conformational isomers are different shapes of the same molecule resulting from rotation around a single $\\ce{C-C}$ bond. They are not different compounds (i.e., they have the same physical and chemical properties) and are readily interconvertible. \n**Conformational isomerism** is a form of stereoisomerism in which the **isomers** can be interconverted just by rotations about single bonds. The different arrangements of atoms caused by rotation about a single bond are called conformations and a compound with a particular conformation is a conformer.\n","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":568,"value":"**Conformations of Ethane ($\\ce{CH3-CH3}$)**\n\nRotation around the $\\ce{C-C}$ bond produces two distinctive conformations. \n1. **Eclipsed Conformation:** $\\ce{C-H}$ bonds on adjacent carbon atoms are parallel to each other.\n \n![](${await FileAttachment('conform1.png').url()})![](${await FileAttachment('conform2.png').url()})\n \n3. **Staggered conformation:** $\\ce{C-H}$ bonds on each carbon atom are as far apart as possible.\n \n![](${await FileAttachment('conform3.png').url()})![](${await FileAttachment('conform4.png').url()})\t\t\t \n\nThe staggered conformation is more stable as the $\\ce{C-H}$ bonds are further apart. The energy difference between them (12 kJ mol$^{−1}$) is known as the *torsional strain*. This energy difference is relatively small, and hence there is free rotation about the $\\ce{C-C}$ bond at room temperature. The angle between the front and back hydrogen is the dihedral (or torsional) angle.\n\t\t\t\t \n![](${await FileAttachment('conform5.png').url()})","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":570,"value":"$4b","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":572,"value":"$4c","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":574,"value":"**Check your understanding 2**\n\n1.\tIdentify if the following 1,4-disubstituted cyclohexane is cis or trans.\n \t\n![](${await FileAttachment('check2-1.png').url()})\n \t\n3.\tDraw two chair conformations for the following cyclohexane derivative\n \t\n![](${await FileAttachment('check2-2.png').url()}) \n","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":576,"value":"**Sources**\n**1.\thttps://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Fundamentals/Isomerism_in_Organic_Compounds/Geometric_Isomerism_in_Organic_Molecules (public domain)**\n**2.\thttps://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_I_(Cortes)/08%3A_Conformational_Analysis_of_Alkanes/8.02%3A_Conformational_Analysis#:~:text=Conformational%20analysis%20is%20the%20study,that%20conformations%20are%20not%20isomers. (public domain)**\n**3.\thttps://kpu.pressbooks.pub/organicchemistry/part/chapter-4-conformations-of-alkanes-and-cycloalkanes/ Creative Commons Attribution-Noncommercial-Share Alike 4.0 International License**\n","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":28,"value":"---","pinned":false,"hidden":false,"mode":"md","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"","database":"$undefined"},{"id":7,"value":"cssstyle","pinned":false,"hidden":false,"mode":"ojs","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"$undefined","database":"$undefined"},{"id":10,"value":"logo","pinned":false,"hidden":false,"mode":"ojs","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"$undefined","database":"$undefined"},{"id":14,"value":"after","pinned":false,"hidden":false,"mode":"ojs","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"$undefined","database":"$undefined"},{"id":5,"value":"import {\n front,\n cssstyle,\n MathJax,\n after,\n logo\n} from \"@yuwang/organicchemistry_imports\"","pinned":false,"hidden":false,"mode":"ojs","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"$undefined","database":"$undefined"},{"id":103,"value":"MathJax","pinned":false,"hidden":false,"mode":"ojs","author":"$undefined","summary":"$undefined","tool":"$undefined","providerMetadata":"$undefined","attachments":"$undefined","output":"$undefined","database":"$undefined"}],"files":"$W4d","stdlib":"1"}} 24:null