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Sn1 Sn2 Multiple Steps Concerted Products are 50% mirrored/inverted and 50% not inverted 100% mirrored/inverted

products RDS is the reactants RDS is the alkyl halide More methyl groups, faster reaction more methyl groups, slower reaction Factors Affecting 3>2>1 - reactivity of alkyl halides 1>2>3 - reactivity of alkyl halides Lower basicity, better leaving group Lower basicity, better leaving group usually run in polar protic solvents accelerated in polar aprotic solvents slowed in polar protic solvents Rearrangement occurs No rearrangement Nucleophile Stronger basicity, strong nucleophilicity Bigger atom, higher polarizability, deacreasing basicity/nucleophilicity, higher nucleophilicity in a protic solvent Nucleophilicity is affected by steric effect; base strength is not Iodide is a great nucleophile despite being a weak base Cyanide is a great nucleophile because of its linear structure Sulfur > oxygen as a nucleophile Elimination Reactions (E2) A hydrogen is removed from a carbon adjacent to the carbon where the halogen is located and a double bond is put in its place Regioselectivity (1 product will predominate): Zaitsev Rule predominating product is obtained when a hydrogen is removed from the carbon where there are fewer hydrogen atoms. Reactivity- 3>2>1 If the base is bulky and approach to the alkyl halide is hindered, base will remove the accessible hydrogen For alkyl fluorides, anti zaitsev rule follows Carbanion stability - 1>2>3 Elimination Reactions (E1) Follows the Zaitsev Rule Increasing size, increasing reactivity for alkyl halides 3>2>1 for substrates (allylic and benzyllic)

Stereochem of E2 and E1 reactions Bonds can be syn periplanar (both h and x are upwards) or anti periplanar (h is upward x is downward) Syn elimination front side attack; anti elimination back side attack E2 reactions involve anti elimination

Alkene with bulkiest groups on opposite sides will have greater yield. (E conformer > Z conformer) E1 reactions follow the same rules as E2 reactions except that both syn and anti elim can occur Elimination from Cyclic Compunds Groups must be in trans. In 6 membered rings, both must be in axial positin Remove the H and X bonds and place a double bond in between E1 Elimination does not have rules Competition between Substitution and Elimination