Which of the following charged nucleophiles is most reactive in $\mathrm{DMSO}$ solvent?

For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol as the solvent). Explain your prediction.

a. (CH₃CH₂)₃N or (CH₃CH₂)₂NH

b. (CH₃)₂O or (CH₃)₂S

For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol as the solvent). Explain your prediction.

g. (CH₃)₂CHO^– or CH₃CH₂CH₂O^–

h. I^– or Cl^–

S_N1 substitution and E1 elimination frequently compete in the same reaction.

b. Compare the function of the solvent (methanol) in the E1 and S_N1 reactions.

Which nucleophile would be more reactive in the solvent given

(c)

Which of the following species is the least nucleophilic?

Which of the following species is most likely to react as a nucleophile rather than as a base?

Which of the following molecules is a negatively charged nucleophile?

Which of the following correctly ranks the nucleophilicity of the species $F_{-}$, ${\mathrm{Cl}}_{-}$, ${\mathrm{Br}}_{-}$, and $I_{-}$ in water from greatest to least?