Which nucleophile would be more reactive in the solvent given
(c)

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

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

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?