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 pointBH3/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