UMass Amherst CHEM 261 - Orgo 1 Review (2 pages)

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Orgo 1 Review

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Pages:
2
School:
University of Massachusetts Amherst
Course:
Chem 261 - Organic Chemistry

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SN2 Substitution Nucleophilic Bimolecular Mechanism Nuc comes in and bonds X bond is broken and free FORMS ONE PRODUCT SN1 Bond to X needs to be broken first and form cation then add nuc SN2 SN1 Electrophile 1 2 3 2 Nucleophile Strong Weak Solvent Aprotic Protic Leaving Group I Br Cl F I Br Cl F Sterochemistry Inversion Racemate 50 50 Mix Rate Law Bimolecular Unimolecular E2 Elimination Bimolecular Mechanism rate k Substrate base H and X Leaving group should be anti coplanar 180 Forms most substituted double bond Zaitsev s rule E1 Elimination Unimolecular mechanism rate k substrate Forms cation and most substituted double bond E2 E1 Electrophile 3 2 1 3 2 Base Strong Weak Solvent Aprotic Protic Leaving Group I Br Cl F I Br Cl F Sterochemistry Antiperiplanar Rate Law Bimolecular unimolecular Alkene NBS Allylic Benzylic Halide Br can be added at any point that is one away from the double bnd KOH Most sub Goes to double bond HCl Double bond broken and Cl added to must sub point BH3 H2O2 OH Breaks double bond and creats a primary alcohol PBr3 Adds Br to LESS sub position H3O Hydration breaks double bond and adds OH mCPBA Double bond breaks and bonds go out at both ends connecting to one O One product coming out one going in O2 Zn H3O Double bond is split in half each half is double bonded to an oxygen KMnO4 H3 Double bond split in half each half is double bonded to an oxygen O also gets added to hydrogen forming OH H2 Pb Catalyst Makes double or triple bonds into single bonds H2 Lindlar Catalyst Triple bond to double bond Cis Alkene Li NH3 Triple bond to double bond Trans alkene



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