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Nucleophilicity Nucleophile strength roughly parallels basicity CH3>NH>OH F Nucleophile strength increases going down a group OH SH F<Cl<Br<I NH;PH3 A base is always a stronger nucleophile than its conjugate acid NH2>NH3 OCH>CH3OHNucleophilicity Nucleophile strength roughly parallels basicity C H3 - > NH2 - > OH- > F- Nucleophile strength increases going down a group O H- < SHF - < Cl- < Br- < IN H3 < PH3 A base is always a stronger nucleophile than its conjugate acid OCH3 - > CH3O H N H2 - > NH3