8. Elimination Reactions

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

(c)

How does the ratio of substitution product to elimination product formed from the reaction of propyl ­bromide with CH₃O⁻ in methanol change if the nucleophile is changed to CH₃S⁻?

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

Which nucleophile would be more reactive in the solvent given?

(b)

Rank the reactivity of the following anions with a general electrophile from least to most reactive.

Which is a better nucleophile?

d. CH₃O⁻ or CH₃OH in DMSO