Show by writing appropriate chemical equations, how the following compounds could be converted to 3-hexyne?
$1 - b u t e n e O s O_{4} - --- \to M e O H N a N H_{2} - ---- \to C H_{3} C H_{2} B r - ------ \to$

Open in App

Solution

1-butene on bromination with $B r_{2} / C C l_{4}$ forms 1,1-dibromobutane.
$C H_{3} C H_{2} C H = C H_{2} + B r_{2} / C C l_{4} \to C H_{3} C H_{2} C H_{2} C H B r_{2}$
When 1,1-dibromobutane is treated with sodaamide , it undergoes dehydrobromination to form 1-butyne.
$C H_{3} C H_{2} C H_{2} C H B r_{2} + N a N H_{2} / N H_{3} d e h y d r o b r o m i n a t i o n - ----------- \to C H_{3} C H_{2} C \equiv C H$
Soda amide abstracts acidic hydrogen atom from 1-butyne.
This is followed by nucleophilic attack on 1-bromoethane to form 3-hexyne.
$C H_{3} C H_{2} - C \equiv C - H + N a N H_{2} \to C H_{3} C H_{2} - C \equiv C^{-} 1 - b r o m o e t h a n e - -------- \to - H B r C H_{3} C H_{2} C \equiv C C H_{2} C H_{3}$

Suggest Corrections

Similar questions

S O_{3}

Write chemical equations for combustion reaction of the following hydrocarbons:

(i) Butane (ii) Pentene (iii) Hexyne (iv) Toluene

Join BYJU'S Learning Program