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

Would you expect the following bases to favor E1 or E2 elimination?

(c)

For each pair, choose the more reactive nucleophile.

(b)

Would you expect methoxide ion to be a better nucleophile if it is dissolved in CH₃OH or if it is dissolved in DMSO? Why?

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.

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