Question

Which one of the following can not be made from 1-bromopropane in a single step?

• A. Propane
• B. Propene
• C. Propan-1-ol
• D. None of the above

Answer 1

Answer: (D)

Propane can be made from $1$-bromopropane in a single step by reduction.
$LiAl{H}_4+4C{H}_{3}C{H}_{2}C{H}_{2}Br\to$
$4C{H}_{3}C{H}_{2}C{H}_3+AlB{r}_3+LiBrLiAl{H}_4$
is a hydride donoar ( $H^{-}$donor).
Note $3^{\circ }$ alkyl halides give alkenes.
Because they undergo dehydrohalogenation.
$C{H}_{3}C{H}_{2}C{H}_{2}Br\underset{\Delta }{\overset{\text{ Alcoholic }KOH}{\to }}$
$C{H}_{3}CH=C{H}_2+KCl+H_{2}O$ (elimination)
$C{H}_{3}C{H}_{2}C{H}_{2}Br\underset{37.3K}{\overset{aq.KOH}{\to }}$
$C{H}_{3}C{H}_{2}C{H}_{2}OH+KBr$ (sublimation)
$C{H}_{3}C{H}_{2}C{H}_{2}Br\underset{\text{in presence of}{C}_2{H}_{5}OH}{\overset{H-N{H}_2,\Delta }{\to }}$
$C{H}_{3}C{H}_{2}C{H}_{2}N{H}_2$ (Substitution)