Question
The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an alkyne. The bromoalkane and alkyne respectively are
A.
$$BrC{H_2}C{H_2}C{H_2}C{H_2}\,{\text{and}}\,C{H_2}C{H_2}C = CH$$
B.
$$BrC{H_2}C{H_2}C{H_3}\,{\text{and}}\,C{H_2}C{H_2}C = CH$$
C.
$$BrC{H_2}C{H_2}C{H_2}C{H_2}C{H_3}\,{\text{and}}\,C{H_3}C = CH$$
D.
$$BrC{H_2}C{H_2}C{H_2}C{H_3}\,{\text{and}}\,C{H_3}C{H_2}C = CH$$
Answer :
$$BrC{H_2}C{H_2}C{H_2}C{H_3}\,{\text{and}}\,C{H_3}C{H_2}C = CH$$
Solution :
$${\text{Only }}\left( {\text{D}} \right){\text{ can form 3}}\,{\text{ - }}\,{\text{Octyne}}$$
\[C{{H}_{3}}C{{H}_{2}}C\equiv CH\xrightarrow[-N{{H}_{3}}]{NaN{{H}_{2}}}\] \[C{{H}_{3}}C{{H}_{2}}C\equiv {{C}^{-}}N{{a}^{+}}\] \[\xrightarrow[\left( {{S}_{N}}2 \right)]{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}Br}C{{H}_{3}}C{{H}_{2}}C\] \[\equiv CC{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{3}}+NaBr\]