Survey of Organic Chemistry
Survey of Organic Chemistry CEM 143
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This 4 page Class Notes was uploaded by Ladarius Rohan on Saturday September 19, 2015. The Class Notes belongs to CEM 143 at Michigan State University taught by Gregory Baker in Fall. Since its upload, it has received 14 views. For similar materials see /class/207692/cem-143-michigan-state-university in Chemistry at Michigan State University.
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Date Created: 09/19/15
CEM 143 Summer 2009 Chapter 6 Concepts Substitution amp Elimination Reactions on Organic Halides Common NucleophilesBases Type Strong Weak Adds substitution only Halogens CI39 Cl Br39 Br I39 Oxygen OH39 H2O OH OH ROH OR Nitrogen NH3 NH3 RN H2 RN H2 RZNH RZNH R3N R3N Sulfur SH39 H28 SH RS39 RSH SR RSR RSR Carbon 39CN HCN CN 39CECR na CECR Strong oxygen nucleophiles typically act as bases Sulfur nucleophiles are slightly stronger than their oxygen counterparts as l39 is a better nucleophile than Br which is better than Cl39 Substitution Reactions SN1 Subsitution nucleophilic unimolecular SN2 Substitution nucleophilic bimolecular What does unimolecular amp bimolecular mean Both reactions happen in two steps however in a unimolecular reaction each of the steps occurs separately whereas in a bimolecular reaction both steps happen simultaneously SN1 Mechanism amp Energetics The carbocation Ratedetermining step intermediate is sp2 LeaVlng group leaVeS hybridized amp therefore flat C LG gt Energy Reaction Progress TS1 Transistion State 1 this is as the leaving group is leaving the C LG bond is breaking T82 Transition State 2 this is as the Nu is attacking the carbocation the CNu bond is forming 8N2 Mechanism amp Energetics Nu39 I 5 l 6 I VG LG gt Nu CLG gt N C NU Transistion State 5 5 Nu cLG Transistion State Energy AC Nu y Reaction Progress