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1Which SN2 reaction is faster?+ CH3CO2NaBrOOA37+ BrBr+ NaOHOH+ Br-BWhy?stronger conjugate acidweaker baseweaker conjugate acidstronger baseIf the atom type (row of periodic table) changes, then nucleophilicity may not be determined by basicity.O HCH3COOH OHbasicitynucleophilicity38SHO HpKa= 167SHHO HHO HCH3COOH OHbasicitynucleophilicityIf the atom type (row of periodic table) changes, then nucleophilicity may not be determined by basicity.39SHO HbasicitynucleophilicityWhy are some species, such as H-Sand Iweak bases andstrong nucleophiles?40SHO HbasicitynucleophilicitySulfur has more polarizable electrons (3s/p) and can form strong bonds at long distances.OHXCRRRHOCRRRXweak bond in transition stateblfi libl41SHXCRRRHSCRRRXbecause sulfur is more polarizablea stronger bond is formed in thetransition stateOHHOCRRRClClCRRR42HSCRRRClClCRRRSH
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