For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).
(a) F^- vs Br^-

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

c. 1-iodobutane

d. CH₃—(CH₂)₃—CN

Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.

e. CH₃—(CH₂)₃—C≡CH

f. CH₃CH₂—O—(CH₂)₃—CH₃

g. CH₃—(CH₂)₃—NH₂

Show how each compound might be synthesized by the SN2 displacement of an alkyl halide.

e. H₂C=CH—CH₂CN

f. H—C≡C—CH₂CH₂CH₃

Give two syntheses for (CH₃)₂CH—O—CH₂CH₃, and explain which synthesis is better.

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(b)

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(d)

Which of the following pairs of substrates will undergo an $S{N}_2$ reaction faster: (A) ${\mathrm{CH}}_3\mathrm{Br}$ vs. ${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{Br}$, (B) ${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{Br}$ vs. ${\mathrm{(CH}}_3{)}_2\mathrm{CHBr}$, (C) ${\mathrm{(CH}}_3{)}_2\mathrm{CHBr}$ vs. ${\mathrm{(CH}}_3{)}_3\mathrm{CBr}$?

Which SN2 reaction in the following pair is faster: (A) $\mathrm{CH}{3}_2\mathrm{CHBr}$ with $\mathrm{OH}-$ or (B) $\mathrm{CH}{3}_3\mathrm{CBr}$ with $\mathrm{OH}-$?