Give the organic product in the following substitution...

Give the organic product in the following substitution reactions. The solvent is given above the arrow. (a) $\mathrm{HS}^{-}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHBrCH}_3 \stackrel{\mathrm{CH}_3 \mathrm{OH}}{\longrightarrow}$ (b) $\mathrm{I}^{-}+\left(\mathrm{CH}_3\right)_3 \mathrm{CBr} \stackrel{\mathrm{HCOOH}}{\longrightarrow}$ (c) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}+\mathrm{AgCN} \longrightarrow 2$ products (d) $\mathrm{CH}_3 \mathrm{CHBrCH}_3+\mathrm{CH}_3 \mathrm{NH}_2 \longrightarrow$ (e) $\mathrm{CH}_3 \mathrm{CHBrCH}_3+\left(\mathrm{CH}_3\right)_2 \ddot{\mathrm{S}}: \longrightarrow$ (f) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}+: \mathrm{P}\left(\mathrm{C}_6 \mathrm{H}_5\right)_3 \longrightarrow$ (g) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}+$ <smiles>[3H][C@H]1CC[Si](O)(O)S1</smiles> (thiosulfate ion) (a) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHSHCH}_3$ (a mercaptan). (b) $\left(\mathrm{CH}_3\right)_3 \mathrm{COCH} ; 3^{\circ} \mathrm{RX}$ undergoes $\mathrm{S}_{\mathrm{N}} 1$ solvolysis. (c) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CN}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{NC} ;: \mathrm{C}=\mathrm{N}$ :- $^{-}$is an ambident anion (Problem 7.24). (d) <smiles>CCCNC(C)C</smiles> $\mathrm{Br}^{-}$; an ammonium salt. (e) $\left[\left(\mathrm{CH}_3\right)_2 \mathrm{CHS}\left(\mathrm{CH}_3\right)_2\right]^{+} \mathrm{Br}^{-}$; a sulfonium salt. (f) $\left[\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{P}\left(\mathrm{C}_6 \mathrm{H}_5\right)_3\right]^{+} \mathrm{Br}^{-}$; a phosphonium salt. $(g)$ <smiles>CCSS(C)([O-])[O-]</smiles> $\mathrm{S}$ is a more nucleophilic site than is $\mathrm{O}$.

Give the organic product in the following substitution reactions. The solvent is given above the arrow.

(a) $\mathrm{HS}^{-}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHBrCH}_3 \stackrel{\mathrm{CH}_3 \mathrm{OH}}{\longrightarrow}$
(b) $\mathrm{I}^{-}+\left(\mathrm{CH}_3\right)_3 \mathrm{CBr} \stackrel{\mathrm{HCOOH}}{\longrightarrow}$
(c) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}+\mathrm{AgCN} \longrightarrow 2$ products
(d) $\mathrm{CH}_3 \mathrm{CHBrCH}_3+\mathrm{CH}_3 \mathrm{NH}_2 \longrightarrow$
(e) $\mathrm{CH}_3 \mathrm{CHBrCH}_3+\left(\mathrm{CH}_3\right)_2 \ddot{\mathrm{S}}: \longrightarrow$
(f) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}+: \mathrm{P}\left(\mathrm{C}_6 \mathrm{H}_5\right)_3 \longrightarrow$
(g) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}+$
<smiles>[3H][C@H]1CC[Si](O)(O)S1</smiles>
(thiosulfate ion)

(a) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHSHCH}_3$ (a mercaptan).
(b) $\left(\mathrm{CH}_3\right)_3 \mathrm{COCH} ; 3^{\circ} \mathrm{RX}$ undergoes $\mathrm{S}_{\mathrm{N}} 1$ solvolysis.
(c) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CN}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{NC} ;: \mathrm{C}=\mathrm{N}$ :- $^{-}$is an ambident anion (Problem 7.24).
(d)
<smiles>CCCNC(C)C</smiles>
$\mathrm{Br}^{-}$; an ammonium salt.
(e) $\left[\left(\mathrm{CH}_3\right)_2 \mathrm{CHS}\left(\mathrm{CH}_3\right)_2\right]^{+} \mathrm{Br}^{-}$; a sulfonium salt.
(f) $\left[\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{P}\left(\mathrm{C}_6 \mathrm{H}_5\right)_3\right]^{+} \mathrm{Br}^{-}$; a phosphonium salt.
$(g)$
<smiles>CCSS(C)([O-])[O-]</smiles>
$\mathrm{S}$ is a more nucleophilic site than is $\mathrm{O}$.

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