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Lewis Theory

An amine on t...

Question

An amine on treatment with ${H N O}_{2}$ evolved $N_{2}$ . The amine on exhaustive methylation with ${C H}_{3} I$ formed a quaternary salt containing 59.07% iodine. The amine is likely to be:

{C H}_{3} {N H}_{2}

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{({C H}_{3})}_{2} N H

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C_{2} H_{5} {N H}_{2}

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{({C H}_{3})}_{3} N

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Solution

The correct option is C $C_{2} H_{5} {N H}_{2}$
c. Evolution of $N_{2}$ with $H N O_{2}$ suggest that $1^{0}$ amine
[either (a) or (c)].
$59.07 g m$ of (I) is present in 100 gm of compound
127 gm of I (1 mol ) in present in $\frac{100 \times 127}{59.07} = 215$
Molecular mass $= 215$
a. $C H_{3} N H_{2} 3 C H_{3} I - --- \to C H_{3} - \oplus N (C H_{3})_{3}] I^{⊖}$
(Molecular mass $= 201$ )
c. $C_{2} H_{5} N H_{2} 3 C H_{3} I - --- \to C_{2} H_{5} - \oplus N (C H_{3})_{3}] I^{⊖}$
(Molecular mass $= 215$ )
Hence, the amine is $C_{2} H_{5} N H_{2} (c)$

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