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Curtius and Hofmann Rearrangements

C2H2→ 3,3- di...

Question

$C_{2} H_{2} \to$ 3,3- dibromohexane

The reagents mentioned below are required to undertake the given reaction.
$R e a g e n t s$ : 1. excess $N a N H_{2}$ 2. excess EtBr 3. Excess HBr

If the statement is true enter 1, else enter 0.

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Solution

$C_{2} H_{2} N a N H_{2} - ---- \to E x c e s s C^{-} \equiv C^{-} C_{2} H_{5} B r - ---- \to E x c e s s C_{2} H_{5} C \equiv C C_{2} H_{5} H B r - --- \to E x c e s s C H_{3} C H_{2} C B r_{2} C H_{2} C H_{2} C H_{3}$

Excess of soda amide abstracts 2 acidic H atoms from acetylene.
This is followed by reaction with 2 moles of ethyl bromide to form 3-hexyne.
In the final step, 2 moles of HBr are added to form 3,3-dibromohexane.
Hence, the given statement is true and the correct answer is 1.

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