Chapter 5 Notes
Chapter 5 Notes CHMY 321-001
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This 2 page Class Notes was uploaded by Ashley Boles on Sunday October 11, 2015. The Class Notes belongs to CHMY 321-001 at Montana State University taught by Holmgren, Steven in Fall 2015. Since its upload, it has received 10 views. For similar materials see Organic Chemistry I in Chemistry and Biochemistry at Montana State University.
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Date Created: 10/11/15
Types of Isomers Constitutional Isomers Same Molecular Formula Different Order of Atom Connectivity W Same Molecular Formula Same Order of Atom Connectivity Differ in Spatial Orientation Enantiomers Conformational Isomers Stereoisomers That Are Nonsuperimposable Stereoisomers That Can Be lnterconverted Mirror Images By Rotation of a BondBonds Diastereoisomers cistrans Isomers Stereoisomers That Are Nonsuperimposable Diastereoisomers With Restricted Rotation NonMirror Images Due to AlkenesCycloalkenes meso Stereoisomers Group of Stereoisomers With Less Than 2n Stereoisomers Due to Reflectional Symmetry Achiral Compounds Due to Plane of Symmetry Nomenclature of Enantiomers 1 Determine the priority of each group coming off the chirality center Higher Atomic Higher Priority In the event of a tie add each subsequent atom until the tie is broken 2 Direct the lowest priority group away from you 3 11213 Clockwise R Configuration 11213 Counterclockwise S Configuration If the lowest priority group is towards you the configuration will be the opposite Chirality Chiral A chiral object or molecule is nonsuperimposable with its mirror image ie has a chirality center Chirality Center Carbon with 4 different substituents attached The number of chirality centers is used to determine the number of possible stereoisomers 2 N P ossible Stereoisomers N Chiralily Centers If a molecule with more than one chirality center has a stereoisomer in which one chirality center stayed the same and one changed the stereoisomer is a diastereomer If a molecule with more than one chirality center has a stereoisomer in which every chirality center changed the molecule is not actually an isomer it is the same molecule Achiral Object or molecule which is superimposable with its mirror image ie has a plane of symmetry Epimers A pair of diastereomers which differ only in the configuration of one atom meso Molecule with 2 chiral centers produces 4 isomers 3 stereoisomers and 1 achiral mirrorplane isomer Optical Activity Based on the ability of a molecule or mixture of molecules to rotate planepolarized light 0 PlanePolarized Light light passing through a grate Specific Rotation is calculated as follows or D 6 Rotated Clockwise Positive Rotated Counterclockwise Negative There is no correlation between rotating and RS configurations Enantiomers when pure rotate planepolarized light in equal and opposite directions 0 This gives zero optical activity when a 5050 mixture of enantiomers is tested which is referred to as a racemic mixture When including optical activity in the nomenclature of enantiomers the is included before the name in parenthesis FisherProjection Diagrams depict chiral3D structure using only straight lines on an axis Groups on the Y axis are equivalent to dashes in a 3D structure going away from the viewer Groups off the X axis are equivalent to wedges in a 3D structure going towards the viewer Determining lsomeric Relationships Same Molecular Formula NC gt Not lsomerically Related YES i Same Order of Connectivity NC Constitutional lsomers YES i Differ in 3D Orientation NC gt Not lsomerically Related YES i Rotate a Bond or Bonds YES Conformational lsomers NO l Nonsuperimposable Mirror Images YES gt Enantiomers NO l Nonsuperimposable NonMirror Images YES Diastereomers YES Restricted Rotation l Presence of AlkenesCycloalkenes YES cistrans lsomers Key Stereoisomers lsomers that differ in spatial orientation
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