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Organic Chemistry 1 Week 5 Notes

by: Jernelle John

Organic Chemistry 1 Week 5 Notes CHEM 231

Marketplace > University of Maryland > Chemistry > CHEM 231 > Organic Chemistry 1 Week 5 Notes
Jernelle John
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About this Document

These are notes from week 5 of organic chemistry lecture and discussion.
Organic Chemistry 1
Dr. Monique Koppel
Class Notes
orgo, Orgo I, Organic Chemistry, Organic Chem, organic, Chemistry
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This 3 page Class Notes was uploaded by Jernelle John on Saturday October 1, 2016. The Class Notes belongs to CHEM 231 at University of Maryland taught by Dr. Monique Koppel in Fall 2016. Since its upload, it has received 7 views. For similar materials see Organic Chemistry 1 in Chemistry at University of Maryland.


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Date Created: 10/01/16
Friday, September 30, 2016 Week 5 Notes Organic Chemistry - Stereoisomers- different compounds with the same molecular formula - Constitutional Isomers aka structural isomers • compounds with the same molecular formula, but different connectivity - Stereoisomers- compounds with the same molecular formula and connectivity, but different 3D spacial arrangement Enantiomers • - non-superimposable mirror images • similar to hands (mirror images, but one hand cannot superimpose itself on the other- will always have either fingers that don’t match up or inside of a palm with outside of a palm- left and right hand will never be the same) • Configurational Isomers- isomers that differ in configuration of the substituents - geometrical isomers- isomers that differ in configuration by means of cis and trans • Diasteriomers- stereoisomers that are not superimposable and are not mirror images of each other - diasteriomers must contain at least two chiral centers - 2 compounds are diasteriomers of each other if the absolute configuration of one isomer is the complete opposite of another isomer • one compound is R, R and the other compound is S, S - Chiral vs. Achiral • chiral molecule- a molecule that contains a chiral carbon - chiral carbon- a carbon atom that contains four different substituent groups • chiral center aka stereocenter - if a molecule has a plane of symmetry (when split in half, is a reflection of the other side of the molecule) than it is not a chiral molecule 1 Friday, September 30, 2016 • achiral molecule- - molecule that does not contain any chiral carbons - racemic mixture- a 50/50 mixture of R and S enantiomers - Cahn Ingold Prelog (CIP) Ranking System- to determine the conformation of a chiral carbon (R or S absolute configuration) • assign priority numbers to substituent groups of chiral carbon based on atomic number - the highest atomic number has the highest priority number - isotopes have a higher priority number than their original atom - if there is a tie (ex. two carbon substituents) move on to the next atom attached until there is a difference in atomic number • double bonds count as two of the same atoms (ex. if there is a carbon-carbon double bond than it counts as C,C when determining priority) • rotate the compound so that the lowest priority number is on a dash • determine the direction based on priority number - the direction from one to two to three - if the direction is clockwise, than we have an R conformation - if the direction is counter-clockwise, than we have an S conformation - n for n chiral centers, 2 stereoisomers maximum are possible - meso compounds- two compounds that are superimposable mirror images of each other • if a compound is meso of another, than it is the same compound n - less than 2 stereoisomers • has a center of symmetry - Fischer projection- diagram of a molecule used when there is more than one chiral center in which… • horizontal lines represent the groups that come out of the page (on wedges in a wedge-dash) 2 Friday, September 30, 2016 • vertical lines represent the groups that go in to the page (on dashes in a wedge- dash model) - If one compound has an R,R configuration, and the other compound has an S,S configuration the two compounds are enantiomers - if one compound has an R,R configuration, and the other compound as an R,S configuration the two compounds are diasteriomers - if one compound has an R,S configuration and the other compound has an S,R configuration than the two compounds are meso compounds 3


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