Question

Place the 3 in A and the 3 in B in order of increasing nucleophility

A. In DMF: CH3CH2ONa, CH3CH2OH, CH3COONa

B. in Methanol: CH3ONa, CH3SNa, CH3OH

Answer 1

A. In DMF: CH3CH2ONa>CH3CH2OH> CH3COONa

In polar aprotic solvents, nucleophilicity of nucleophiles increases because With the same nucleophilic atom, same charge type, nucleophilicity parallels basicity

B. in Methanol: CH3ONa <CH3SNa <CH3OH

In polar protic solvents, the nucleophlicity decreasesbecause Polar, protic solvents such as water and alcohols solvate anions by hydrogen bonding interactions. These solvated species are more stable and less reactive than the unsolvated "naked" anions.