Aliphatic Compounds Containing Nitrogen - Result Question 35

####37. A basic volatile nitrogen compound gave a foul smelling gas when treated with chloroform and alcoholic KOH. A 0.295g sample of the substance dissolved in aq. HCl and treated with NaNO2 solution at 0C, liberated a colourless, odourless gas whose volume corresponds to 112mL at STP.

After evolution of the gas was complete, the aqueous solution was distilled to give an organic liquid which did not contain nitrogen and which on warming with alkali and iodine gave a yellow precipitate. Identify the original substance assuming that it contains one N-atom per molecule.

(1993,4M)

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Solution:

  1. Starting compound is a primary amine.

RNH2+CHCl3+KClRNC foul smell 

Also, RNH2+HNO2ROH+N2

Moles of N2=11222500=5×103

One mole of N2 is obtained from 1.0 mole of RNH2, mole of RNH2=5×103

5×103molRNH2 weigh =0.295g

1 mole of RNH2 will weigh =0.2955×103=59g

In RNH2,NH2 has molar mass =16

R - has molar mass =43

Also, the alcohol ROH gives iodoform test; it must has the following skeleton :

RCHOHCH3

R - has molar mass =15(CH3)

Original compound is CH3C+CHNH2



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