What are ambident nucleophiles? Explain with an example.

Which compound in each of the following pairs will react faster in ${\mathrm{S}}_{{\mathrm{N}}^2}$ reaction with ${\mathrm{OH}}^{-}$?

(a) ${\mathrm{CH}}_3\mathrm{Br}$ or ${\mathrm{CH}}_3\mathrm{I}$

(b) ${\left({\mathrm{CH}}_3\right)}_3\mathrm{CCl}$ or ${\mathrm{CH}}_3\mathrm{Cl}$

Explain the following reaction:

$\mathrm{n}-\mathrm{BuBr}+\mathrm{KCN}\stackrel{\mathrm{EtOH}-{\mathrm{H}}_2\mathrm{O}}{⟶}\mathrm{n}-\mathrm{BuCN}+\mathrm{KBr}$

Complete the following by providing $\left(\mathrm{A}\right),\left(\mathrm{B}\right),\left(\mathrm{C}\right)$ and $\left(\mathrm{D}\right)$

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH}\stackrel{{\mathrm{PBr}}_3}{⟶}\left(\mathrm{A}\right)\stackrel{\mathrm{alc}.\mathrm{KOH}}{⟶}\left(\mathrm{B}\right)\stackrel{\mathrm{HBr}}{⟶}\left(\mathrm{C}\right)\stackrel{{\mathrm{NH}}_3}{⟶}\left(\mathrm{D}\right)$

Give reasons: iodoform is obtained by the reaction of acetone with hypoiodite but not with iodide ion.

${\mathrm{CH}}_3\mathrm{C}\equiv {\mathrm{C}}^{-}{\mathrm{Na}}^{+}+{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Cl}$

Supply formulae for the organic products from the reaction of:

${\mathrm{CH}}_3\mathrm{CHCl}.{\mathrm{CH}}_2{\mathrm{CH}}_3+{\mathrm{NaOH}}_{\left(\mathrm{aq}\right)}$

Supply formulae for the organic products from the reaction of:

${\left({\mathrm{CH}}_3\right)}_2{\mathrm{CHO}}^{-}{\mathrm{Na}}^{+}+{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Cl}$

Supply formulae for the organic products from the reaction of:

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Br}+{\mathrm{Me}}_2 \mathrm{S}$