6. Which substance in each of the following pairs is more reactive as a nucleophile? Why? a. (CH3)2N- or (CH3)2NH, b. (CH3)3B or (CH3)3N c. H2O or H2S
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(CH3)3N- or (CH3)3NH: The negative charge on the nitrogen in (CH3)3N- makes it a stronger nucleophile compared to (CH3)3NH, which has a neutral charge. The negative charge increases the electron density around the nitrogen, making it more likely to donate Show more…
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Which reactant in each of the following pairs is more nucleophilic? Explain. (a) $-\mathrm{NH}_{2}$ Or $\mathrm{NH}_{3}$ (c) $\mathrm{BF}_{3}$ or $\mathrm{F}^{-}$ (e) $\mathrm{I}^{-}$ or $\mathrm{Cl}^{-}$ (b) $\mathrm{H}_{2} \mathrm{O}$ or $\mathrm{CH}_{3} \mathrm{CO}_{2}^{-}$ (d) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{P}$ or $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}$ (f) $-\mathrm{C} \equiv \mathrm{N}$ or $^{-} \mathrm{OCH}_{3}$
Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (a) $\mathrm{CH}_{3} \mathrm{NH}$ or $\mathrm{CH}_{3} \mathrm{NH}_{2}$ (b) $\mathrm{CH}_{3} \mathrm{O}^{-}$ or $\mathrm{CH}_{3} \mathrm{CO}_{2}^{-}\left(^{-} \mathrm{OAc}\right)$ (c) $\mathrm{CH}_{3} \mathrm{SH}$ or $\quad \mathrm{CH}_{3} \mathrm{OH}$ (d) $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{N} \quad$ or $\quad\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{P}$ (e) $\mathrm{H}_{2} \mathrm{O} \quad$ or $\quad \mathrm{H}_{3} \mathrm{O}^{+}$ (f) $\mathrm{NH}_{3}$ or $^{+} \mathrm{NH}_{4}$ (g) $\mathrm{H}_{2} \mathrm{S}$ or $\mathrm{HS}^{-}$ (h) $\mathrm{CH}_{3} \mathrm{CO}_{2}^{-}\left(^{-} \mathrm{OAc}\right)$ or $\mathrm{HO}^{-}$
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