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Standard XII

Chemistry

Sigma Bond and Pi Bond

Compound A ...

Question

Compound $A [C_{4} H_{8} N_{2}]$ on hydrolysis in acidic medium gave $B$ ( $[C_{4} H_{9} O_{2} N]$ ). A on reduction with $L i A l H_{4}$ gave $C$ $([C_{4} H_{12} N_{2}])$ .'B' on treatment with $N a H C O_{3}$ solution liberates $C O_{2}$ . 'B' on heating forms $D$ ( $[C_{4} H_{7} O N]$ ). 'D' on reduction with $L i A l H_{4}$ forms secondary amine $E$ ( $[C_{4} H_{9} N]$ ). Number of single bonds in final compound E are:

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Solution

' $A$ ' undergoes hydrolysis in acid medium to give $B$ . Since one nitrogen is lost and $- O O H$ is added in this reaction $- C N$ group must be present in ' $A$ '.
$A C_{4} H_{8} N_{2} L i A l H_{4} - --- \to 4 (H) C C_{4} H_{12} N_{2}$

$B C_{4} H_{9} O_{2} N - H_{2} O - --- \to h e a t D C_{4} H_{7} O N$

$D C_{4} H_{7} O N L i A l H_{4} - --- \to 4 H E C_{4} H_{9} N + H_{2} O$
secondary amine

This also indicates the presence of $- C N$ group in ' $A$ '.
'B' must be a carboxylic acid as it liberates $C O_{2}$ from $N a H C O_{3}$ solution.
Thus, the second nitrogen is in the form of $- N H_{2}$ and $D$ will be a cyclic amide.
[ $γ$ -amino acid forms cyclic amide on heating].

Thus $A$ must be $C | H_{2} N H_{2} - C H_{2} - C H_{2} - C N$
The reactions are
$H_{2} N - C H_{2} - C H_{2} - C H_{2} - C N [A] H_{3} O^{=} - -- \to H_{2} N - C H_{2} - C H_{2} - C H_{2} - C O O H [B]$
Here, it can be seen that final compound $E$ contains, 14 single bonds

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