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:

B r C H_{2} C H_{2} C H_{2} C H_{2} C H_{3}

and

C H_{3} C H_{2} C = C H

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B r C H_{2} C H_{2} C H_{3}

and

C H_{3} C H_{2} C H_{2} C = C H

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B r C H_{2} C H_{2} C H_{2} C H_{2} C H_{3}

and

C H_{3} C = C H

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B r C H_{2} C H_{2} C H_{2} C H_{3}

and

C H_{3} C H_{2} C = C H

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Solution

The correct option is D $B r C H_{2} C H_{2} C H_{2} C H_{3}$ and $C H_{3} C H_{2} C = C H$
${C H}_{3} {C H}_{2} {C H}_{2} {C H}_{2} B r a n d {C H}_{3} {C H}_{2} C \equiv C H 1 - B r o m o b u t a n e 1 - B u t y n e {C H}_{3} {C H}_{2} C \equiv C H {N a N H}_{2} - ---- \to {C H}_{3} {C H}_{2} {C \equiv C}^{-} {N a}^{+} {C H}_{3} {C H}_{2} {C \equiv C}^{-} {N a}^{+} + {B r C H}_{2} {C H}_{2} {C H}_{2} {C H}_{3} \to {C H}_{3} {C H}_{2} {C H}_{2} {C H}_{2} C \equiv C {C H}_{2} {C H}_{3} + N a B r 3 - O c t y n e$

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3 - o c t y n e

C H_{3} C H_{2} C \equiv C H (i) N a N H_{2}, N H_{3} - --------- \to (i i) C H_{3} C H_{2} B r H_{2} - ------------ \to L i n d l a r^{'} s c a t a l y s t, P d C H_{2} I_{2} - --- \to Z n (C u)

B (m i x) c o n c . H I \leftarrow ---- - (C H_{3})_{3} C - O - C H_{3} a n h y d H I - ----- \to A (m i x)

C h_{3} C = C - C H_{3}

C H_{3} C H_{2} - C H_{2} - C H_{3}

C H_{3} C H_{2} C = C H

C H_{3} C H = C H_{2}

$B (m i x) C o n c . H I ⟵ ((C H_{3})_{3} C - O - C H_{3}) a n h y d . H I \to A (m i x)$

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